[ CAS No. 141-28-6 ] {[proInfo.proName]}

Name: 141-28-6|Diethyl adipate|95%
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Quality Control of [ 141-28-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 141-28-6 ]

Product Details of [ 141-28-6 ]

CAS No. :	141-28-6	MDL No. :	MFCD00009215
Formula :	C₁₀H₁₈O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VIZORQUEIQEFRT-UHFFFAOYSA-N
M.W :	202.25	Pubchem ID :	8844
Synonyms :

Calculated chemistry of [ 141-28-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.8
Num. rotatable bonds :	9
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.75
TPSA :	52.6 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.67
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	1.67
Log Po/w (MLOGP) :	1.55
Log Po/w (SILICOS-IT) :	2.01
Consensus Log Po/w :	1.9

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.51
Solubility :	6.28 mg/ml ; 0.0311 mol/l
Class :	Very soluble
Log S (Ali) :	-2.32
Solubility :	0.977 mg/ml ; 0.00483 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.47
Solubility :	0.69 mg/ml ; 0.00341 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.87

Safety of [ 141-28-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P273-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335-H412	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 141-28-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 141-28-6 ]
Downstream synthetic route of [ 141-28-6 ]

[ 141-28-6 ] Synthesis Path-Upstream 1~4

1
[ 141-28-6 ]
[ 1071-93-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With hydrazine hydrate In ethanol at 75℃; for 5 h;	General procedure: 7.6 g (100.0 mmol) of solid hydrazine (H3N + NHCO2-) and adipic acid (7.3 g, 50.0 mmol) were mixed in a mortar without a solvent for 10 minutes and stirred at 100 ° C for 5 hours. To confirm the structure and composition of the product produced in this process and analyzed using 400 MHz NMR (nuclear magnetic resonance) and elemental analysis) .As a result of the analysis, the product was adipohydrazide (C6H14N4O2), the conversion rate was 96percent or more, and the yield was 95percent or more. Yield (8.27 g, 96percent or more); The product was obtained in the same manner as in Example 1 except that 10 g of decane was used as a solvent and stirred at 110 DEG C for 12 hours and filtration and separation were carried out. The filtration and separation processes were carried out according to a known method. As a result of analysis on the product, the product was adipohydrazide (C6H14N4O2), the conversion was 97percent, and the yield was 93percent. 5.0 g (100.0 mmol) of hydrazine hydrate was used instead of the solid hydrazine and 10.12 g (100.0 mmol) of diethyl adipate was used instead of adipic acid.The product was obtained in the same manner as in Example 3 except that 10 g of ethanol was used as a solvent and the mixture was stirred at 75°C for 5 hours. As a result of analysis of the product, the product was adipohydrazide (C6H14N4O2), the conversion was 89percent, and the yield was 83percent.

Reference： [1] Patent: KR2015/88523, 2015, A, . Location in patent: Paragraph 0128; 0137; 0148-0149
[2] Organic Syntheses, 1956, vol. 36, p. 72,Note 7
[3] Justus Liebigs Annalen der Chemie, 1929, vol. 475, p. 122
[4] Journal fuer Praktische Chemie (Leipzig), 1915, vol. <2> 91, p. 23
[5] Journal fuer Praktische Chemie (Leipzig), 1981, vol. 323, # 3, p. 360 - 366
[6] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1988, vol. 27, # 3, p. 225 - 230
[7] Russian Journal of Applied Chemistry, 2001, vol. 74, # 8, p. 1348 - 1352
[8] Journal of Coordination Chemistry, 2011, vol. 64, # 2, p. 300 - 313
[9] Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2012, vol. 74, # 1-4, p. 257 - 263
[10] Journal of Molecular Structure, 2015, vol. 1092, p. 122 - 129

2
[ 141-28-6 ]
[ 629-03-8 ]

Reference： [1] Monatshefte fuer Chemie, 1927, vol. 48, p. 524,729

3
[ 42367-85-1 ]
[ 539-82-2 ]
[ 1968-40-7 ]
[ 141-28-6 ]
[ 110-40-7 ]

Reference： [1] Helvetica Chimica Acta, 1935, vol. 18, p. 449

4
[ 141-28-6 ]
[ 1194-18-9 ]

Reference： [1] Synthesis, 1996, # 4, p. 525 - 528

[ 141-28-6 ] Synthesis Path-Downstream 1~49

1
[ 124-04-9 ]
[ 64-17-5 ]
[ 626-86-8 ]
[ 141-28-6 ]

Yield	Reaction Conditions	Operation in experiment
65%; 35%	With Diethyl carbonate; at 180℃; under 10343.2 Torr; for 5h;Inert atmosphere;	Example A; Synthesis of Diethyiadipate from Adipie Acid, Die ycarbonate, and Ethanol H)0% cooversiofs 35% Cd 6S% yield Twnty grams adipie acid, 83 mL of diethy (carbonate, and 300 g of ethanol were charged to a stainless steel, 1.1, Parr reactor body. While stirring .mechanically at 1 00 rpm, the internal headspace was pressurized to 200 psi :, and heated to 1 WC for 5h. After this time, the reactor body was cooled in a water bath until reaching room temperature and pressure released. The homogeneous solution was poured into a storage flask and a sample of this quantitatively analyzed for diethyladipate, mono-methyiadipate and adipie acid.

Reference： [1]Patent: WO2014/70415,2014,A1 .Location in patent: Page/Page column 10
[2]Bulletin des Societes Chimiques Belges,1926,vol. 35,p. 188
Chemisches Zentralblatt,1926,vol. 97,p. 1126

2
[ 124-04-9 ]
[ 64-17-5 ]
[ 141-28-6 ]

Yield	Reaction Conditions	Operation in experiment
95.7%	With zeolite;	Add 2 g of zeolite to a three-necked flask.At the same time, 30g Mg2+ loaded resin catalyst is loaded on the upper part of the tower.Then, 146 g of adipic acid and 365 g of ethanol accurately weighed by an electronic balance were added to a conical flask to form a mixed mass of a certain mass ratio.Pour into the tower kettle;Step 2, the tower top condenser cooling water switch and the tower kettle control power supply are set, the heating rate is set to 5 C / min, and the acid value before the reaction is determined by using the calibrated NaOH standard solution;Step 3: After the reflux occurs at the top of the tower, after 20 minutes of stabilization, the top constant pressure funnel starts to feed, and the reflux ratio control switch is turned on.The reflux ratio is controlled to 1, and the timing starts, and the reaction starts;Step 4. When the top of the column is fed, the reaction is over, and the reaction time is recorded. At this time, the tower pressure is increased.Distilling excess methanol in the reaction system to purify the product,When the temperature at the bottom of the tower rises to 110 C, stop heating and turn off the power;Step 5,After 2h,The retentate in the column was refluxed, and the three-barrel flask was cooled, and then distilled under reduced pressure at 4.0 Kpa.Collecting 148-152 C fraction to obtain liquid diethyl adipate;
	With acidic cation exchange resin Amberlyst 70; at 50 - 160℃;Flow reactor; Green chemistry;	General procedure: Hexanedioic acid and methanol at a weight ratio of 1:5 were mixed at 50 C., and then introduced into the lower part of the vertical reactor at a liquid hourly space velocity (LHSV) of 6 hour-1. The reaction was performed at 130 to 175 C., as shown in Table 2. The reaction was performed at 115 C.. The esterized mixture was output from the upper part of the vertical reactor, and collected to be analyzed by gas photography. The acid value of the product was determined by titration, and the conversion rate and the selectivity were analyzed. The results were shown in Table 2.
260 g	With sulfuric acid; at 0℃;Reflux;	Adipic acid (200 g) and ethanol (1,200 mL) were added to a 2 L three-necked flask equipped with a condenser, and 20 mL of sulfuric acid was slowly added at 0 C.The reaction solution was stirred overnight while refluxing, then the solution was concentrated to about 1/3, and the reaction mixture was gradually poured into 400 mL of saturated aqueous sodium hydrogen carbonate solution.After confirming that the pH was neutral, the aqueous layer was extracted three times with 400 mL of ethyl acetate, and all the organic layers were combined and washed with 600 mL of saturated sodium bicarbonate and 600 mL of saturated brine.The obtained organic layer was dried over Na2SO4, and then the solvent was distilled off to obtain 260 g of diethyl adipate.In addition, the identification of diethyl adipate was performed by NMR analysis.

260 g

With sulfuric acid; In ethanol; at 0℃;Reflux;

Adipic acid 200 g and ethanol 1,200 mL were added to a 2 L three-necked flask equipped with a condenser, and 20 mL of sulfuric acid was slowly added at 0 C.After the reaction solution was refluxed and stirred overnight, the solution was concentrated to about 1/3, and the reaction mixture was gradually poured into 400 mL of saturated aqueous sodium hydrogen carbonate solution.After confirming that the pH was neutral, the aqueous layer was extracted three times with 400 mL of ethyl acetate, and all the organic layers were combined and washed with 600 mL of saturated sodium bicarbonate and 600 mL of saturated brine.The obtained organic layer was dried over Na 2 SO 4 and then the solvent was distilled off to obtain 260 g of diethyl adipate.Note that diethyl adipate was identified by NMR analysis.

Reference： [1]Synthetic Communications,1998,vol. 28,p. 1159 - 1162
[2]Patent: CN109704969,2019,A .Location in patent: Paragraph 0007; 0008; 0009-0025
[3]Synthetic Communications,1992,vol. 22,p. 1087 - 1094
[4]Journal of Organic Chemistry,1983,vol. 48,p. 3598 - 3600
[5]Journal of Organic Chemistry,1983,vol. 48,p. 3106 - 3108
[6]Bulletin de la Societe Chimique de France,1927,vol. <4>41,p. 446 Anm. 8
[7]Journal fur praktische Chemie (Leipzig 1954),1865,vol. <1> 95,p. 206
    Zeitschrift fuer Chemie,1865,p. 301
[8]Bulletin de la Societe Chimique de France,1937,vol. <5> 4,p. 1667
[9]Chemisches Zentralblatt,1927,vol. 98,p. 268
[10]Rikagaku Kenkyusho Iho,1943,vol. 22,p. 476
    Chem.Abstr.,1948,p. 1205
[11]Bulletin de la Societe Chimique de France,1908,vol. <4>3,p. 443,447
    Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1908,vol. 146,p. 84,139
[12]Journal of Chemical and Engineering Data,2011,vol. 56,p. 800 - 810
[13]Patent: US2013/303796,2013,A1 .Location in patent: Paragraph 0027; 0029; 0034
[14]Green Chemistry,2016,vol. 18,p. 2193 - 2200
[15]Patent: JP2019/142782,2019,A .Location in patent: Paragraph 0038; 0039
[16]Patent: JP2019/142783,2019,A .Location in patent: Paragraph 0054; 0055

3
[ 6414-69-3 ]
[ 141-28-6 ]

Reference： [1]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1914,vol. 46,p. 502
Chemisches Zentralblatt,1914,vol. 85,p. 1269

4
[ 141-28-6 ]
[ 629-11-8 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1980,vol. 16,p. 1728 - 1733
    Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 2032 - 2038
[2]Journal of the American Chemical Society,1948,vol. 70,p. 3121
[3]Organic Syntheses, Collective,
[4]Monatshefte fur Chemie,1927,vol. 48,p. 524,729
[5]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1903,vol. 137,p. 328
    Bulletin de la Societe Chimique de France,1904,vol. <3>31,p. 1208
    Chemisches Zentralblatt,1905,vol. 76,p. 1700
[6]Journal of the American Chemical Society,1934,vol. 56,p. 2419,2422
[7]Patent: DE164294,
[8]Patent: US2079414,1932,

5
[ 141-28-6 ]
[ 626-86-8 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1528 - 1536
[2]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1936,vol. 242,p. 186
[3]Biochemical Journal,1928,vol. 22,p. 193

6
[ 141-28-6 ]
[ 611-10-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium methylate; at 150℃;	Example 2; The process was carried out in a corotating twin-shaft extruder model ZSK34 having a shaft diameter of 34 mm. The process section of the machine had a length of 1560 mm. The machine was provided with an opening for the introduction of solids. The liquid was introduced via a drilled hole in the barrel. Mixing of the components is effected by the kneading elements located on the shaft. The volatile reaction products were taken off via an open venting facility. 1.31 kg/h of sodium methoxide as powder and 3.69 kg/h of <strong>[141-28-6]diethyl adipate</strong> as liquid were metered into the machine. The rotational speed of the machine was about 60 l/min. The mixture was heated to about 150 C. by means of the barrel heating. At the end of the machine, a crumbly white solid was discharged. After acidification, aqueous work-up and extraction with an organic solvent (toluene), no starting material in the form of <strong>[141-28-6]diethyl adipate</strong>, monomethyl adipate or adipic acid could be detected. Only ethyl cyclopentanone-2-carboxylate was found. The yield based on <strong>[141-28-6]diethyl adipate</strong> was quantitative.
~ 99%	With sodium ethanolate; at 120℃; under 7.50075 Torr; for 0.75h;	Example 1; The process was carried out in a high-viscosity reactor model CRP 2,5 Batch from List AG. The high-viscosity reactor is a machine having two horizontal corotating mixing shafts. Kneading devices which intermesh and thus ensure rapid and homogeneous mixing are located on the shafts. In addition, the machine has a discharge screw by means of which the product can be conveyed out of the reaction chamber. It can be operated continuously or batchwise. The reactor has a free volume of about 2.5 l. The reaction chamber of the machine can be heated. Volatile constituents can be taken off via a vent. 1336 g of <strong>[141-28-6]diethyl adipate</strong> and 472 g of sodium ethoxide were placed in the high-viscosity reactor. After start-up of the kneader and commencement of mixing of the starting materials a viscous mass was immediately formed. While kneading slowly, the temperature was slowly increased to 120 C. A vacuum of 10 mbar was slowly built up. The temperature of 120 C. was reached after about 15 minutes. Slow kneading was then continued at a temperature of 120 C. for 30 minutes until a pulverized white solid had been obtained. The powder formed was discharged by means of a transport screw and subsequently hydrolysed using half-strength sulphuric acid. Phase separation and distillation at 120 C./10 mbar gave 1021 g of ethyl cyclopentanone-2-carboxylate, viz. about 99% of theory. Diethyl adipate could no longer be detected.
85.6%		EXAMPLE 25 Preparation of 2-methylene-5-diphenylmethylenecyclopentanone Step A: Preparation of cyclopentanone-2-carboxylic acid ethyl ester 15.0 g (0.652 mmol) of sodium was placed in 150 mL toluene, heated to reflux, shaken, and made into sodium sand. 81.6 g (0.400 mol) of <strong>[141-28-6]diethyl adipate</strong> was added in drops to the mixture in an outside bath at 105-110C, and the resultant solution changed into a yellow sticky product. After refluxing for 8 h, the solution was cooled by ice bath, and 400 mL of 10% acetic acid solution was added in drops. The mixture was suction filtered and washed with a small amount of toluene. The filtrate was separated into layers. The upper layer was washed with 7% sodium carbonate (260 mL×2) followed by saturated brine (200 mLx2), and dried overnight with anhydrous magnesium sulfate. The solution was filtered, concentrated and distilled under reduced pressure to collect the fractions of bp:142-150C/2660Pa, yielding 53.3 g of colorless liquid with a yield of 85.6%.

85.6%

With sodium; In toluene; at 105 - 110℃; for 8h;

Example 25; Preparation of 2-methylene-5-diphenylmethylenecyclopentanone; Step A: Preparation of cyclopentanone-2-carboxylic acid ethyl ester 15.0 g (0.652 mmol) of sodium was placed in 150 mL toluene, heated to reflux, shaken, and made into sodium sand. 81.6 g (0.400 mol) of <strong>[141-28-6]diethyl adipate</strong> was added in drops to the mixture in an outside bath at 105-110 C., and the resultant solution changed into a yellow sticky product. After refluxing for 8 h, the solution was cooled by ice bath, and 400 mL of 10% acetic acid solution was added in drops. The mixture was suction filtered and washed with a small amount of toluene. The filtrate was separated into layers. The upper layer was washed with 7% sodium carbonate (260 mL*2) followed by saturated brine (200 mL*2), and dried overnight with anhydrous magnesium sulfate. The solution was filtered, concentrated and distilled under reduced pressure to collect the fractions of bp: 142-150 C./2660 Pa, yielding 53.3 g of colorless liquid with a yield of 85.6%.

Reference： [1]Patent: US2006/79709,2006,A1 .Location in patent: Page/Page column 4
[2]Patent: US2006/79709,2006,A1 .Location in patent: Page/Page column 3-4
[3]Journal of the Chemical Society. Perkin transactions I,1998,p. 3521 - 3522
[4]Tetrahedron,1998,vol. 54,p. 10827 - 10836
[5]Patent: EP2248796,2010,A1 .Location in patent: Page/Page column 16-17
[6]Patent: US2011/60054,2011,A1 .Location in patent: Page/Page column 12
[7]Tetrahedron Letters,1984,vol. 25,p. 753 - 756
[8]Chemische Berichte,1894,vol. 27,p. 103
Justus Liebigs Annalen der Chemie,1901,vol. 317,p. 47,93
[9]Bulletin de la Societe Chimique de France,1899,vol. <3> 21,p. 1022
[10]Justus Liebigs Annalen der Chemie,1901,vol. 317,p. 104
[11]Journal of the Chemical Society,1934,p. 935,942
[12]Acta Chemica Scandinavica (1947),1948,vol. 2,p. 385,386
[13]Journal of the Chemical Society,1934,p. 935,942
[14]Bulletin of the Chemical Society of Japan,1996,vol. 69,p. 2619 - 2624
[15]Journal of the Serbian Chemical Society,2013,vol. 78,p. 759-768+S57-S61
[16]RSC Advances,2014,vol. 4,p. 44350 - 44358

7
[ 141-28-6 ]
[ 1071-93-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With hydrazine hydrate; In ethanol; at 75℃; for 5h;	General procedure: 7.6 g (100.0 mmol) of solid hydrazine (H3N + NHCO2-) and adipic acid (7.3 g, 50.0 mmol) were mixed in a mortar without a solvent for 10 minutes and stirred at 100 C for 5 hours. To confirm the structure and composition of the product produced in this process and analyzed using 400 MHz NMR (nuclear magnetic resonance) and elemental analysis) .As a result of the analysis, the product was adipohydrazide (C6H14N4O2), the conversion rate was 96% or more, and the yield was 95% or more. Yield (8.27 g, 96% or more); The product was obtained in the same manner as in Example 1 except that 10 g of decane was used as a solvent and stirred at 110 DEG C for 12 hours and filtration and separation were carried out. The filtration and separation processes were carried out according to a known method. As a result of analysis on the product, the product was adipohydrazide (C6H14N4O2), the conversion was 97%, and the yield was 93%. 5.0 g (100.0 mmol) of hydrazine hydrate was used instead of the solid hydrazine and 10.12 g (100.0 mmol) of <strong>[141-28-6]diethyl adipate</strong> was used instead of adipic acid.The product was obtained in the same manner as in Example 3 except that 10 g of ethanol was used as a solvent and the mixture was stirred at 75C for 5 hours. As a result of analysis of the product, the product was adipohydrazide (C6H14N4O2), the conversion was 89%, and the yield was 83%.
	With hydrazine hydrate; In ethanol; for 0.5h;Reflux;	Preparation of bis(2-hydroxy-1-naphthaldehyde)adipoyldihydrazone Adipoyldihydrazide was prepared by reacting <strong>[141-28-6]diethyl adipate</strong> (1.00 g) with hydrazine hydrate (0.55 g) in 1:2 molar ratio in 20 mL ethanol under reflux for 30 mins. The product was recrystallized from dilute ethanol.

Reference： [1]Patent: KR2015/88523,2015,A .Location in patent: Paragraph 0128; 0137; 0148-0149
[2]Organic Syntheses,1956,vol. 36,p. 72,Note 7
[3]Justus Liebigs Annalen der Chemie,1929,vol. 475,p. 122
[4]Journal fur praktische Chemie (Leipzig 1954),1981,vol. 323,p. 360 - 366
[5]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1988,vol. 27,p. 225 - 230
[6]Russian Journal of Applied Chemistry,2001,vol. 74,p. 1348 - 1352
[7]Journal of Coordination Chemistry,2011,vol. 64,p. 300 - 313
[8]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2012,vol. 74,p. 257 - 263
[9]Journal of Molecular Structure,2015,vol. 1092,p. 122 - 129

8
[ 42367-85-1 ]
[ 539-82-2 ]
[ 1968-40-7 ]
[ 141-28-6 ]
[ 110-40-7 ]

Reference： [1]Helvetica Chimica Acta,1935,vol. 18,p. 449

9
[ 75-77-4 ]
[ 141-28-6 ]
[ 6838-67-1 ]

Yield	Reaction Conditions	Operation in experiment
88.6%	With benzophenone; sodium; In toluene; at 50℃;Inert atmosphere;	1), under dry nitrogen protection,After adding 800 ml of dry solvent toluene and 0.1 g of benzophenone to the 2000 ml three-necked flask, 3680 g (1.6 mol) of metallic sodium was added in portions. After the mixture was sufficiently stirred, the solution in the reaction bottle was dark blue;2), and then the temperature was raised to 50 C, and then 80.90 g (0.4 mol)<strong>[141-28-6]1,6-hexanedioic acid diethyl ester</strong> and 130.37 g (1.6 mol) of trimethylchlorosilane;3), drop at 50 C for 3 to 4 hours, wait until the dark blue of the reaction solution completely disappears and then stir for 1 hour; stop stirring, filter out insoluble matter NaCl (about 93.56g after drying);4), the filtrate was concentrated, and the by-product trimethylethoxysilane (TMSOEt, about 94.55 g, boiling point 75-76 C) and solvent toluene were distilled off successively;5), followed by vacuum distillation,A fraction of 102-105 C / 10-12 mmHg was collected to give 91.61 g (0.35 mol) of product 1,2-bis-trimethylsiloxycyclohexene (enol silicon ether) in 88.6% yield, 98% purity ( GC analysis).

Reference： [1]Patent: CN104592284,2017,B .Location in patent: Paragraph 0018; 0023; 0025-0030; 0032-0044
[2]Synthetic Communications,1980,vol. 10,p. 415 - 420
[3]Journal of Organic Chemistry,1985,vol. 50,p. 3411 - 3414
[4]Synthesis,1996,p. 525 - 528
[5]Synlett,1997,vol. 1997,p. 267 - 268
[6]Tetrahedron,1998,vol. 54,p. 10827 - 10836
[7]Synthesis,1971,p. 236 - 253
[8]Canadian Journal of Chemistry,1977,vol. 55,p. 757 - 765
[9]Chemische Berichte,1964,vol. 97,p. 1383 - 1389

10
[ 141-28-6 ]
[ 74-88-4 ]
[ 5453-88-3 ]

Reference： [1]Canadian Journal of Chemistry,1962,vol. 40,p. 353 - 366
[2]Journal of Organic Chemistry,2003,vol. 68,p. 9226 - 9232

11
[ 64-17-5 ]
[ 55-98-1 ]
[ 201230-82-2 ]
[ 141-28-6 ]

Reference： [1]Tetrahedron Letters,1991,vol. 32,p. 3091 - 3094

12
[ 869-10-3 ]
[ 141-28-6 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 5400 - 5405

13
[ 869-10-3 ]
[ 141-28-6 ]
[ 7209-01-0 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 5400 - 5405

14
[ 141-28-6 ]
[ 1072-21-5 ]

Reference： [1]Journal of Organic Chemistry,1987,vol. 52,p. 5486 - 5487
[2]Organic Preparations and Procedures International,1995,vol. 27,p. 95 - 98
[3]Organic Preparations and Procedures International,1992,vol. 24,p. 335 - 337

15
[ 141-28-6 ]
[ 125541-07-3 ]
[ 611-10-9 ]

Reference： [1]Journal of the American Chemical Society,1990,vol. 112,p. 1660 - 1661

16
[ 627-93-0 ]
[ 105-53-3 ]
[ 6186-89-6 ]
[ 141-28-6 ]
[ 18891-13-9 ]
[ 108-59-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 2.6 g 2: 1.5 g 3: 4.8 g 4: 2 g	With iron pentacarbonyl; iodine at 135℃; for 3h;

Reference： [1]Velichko, F. K.; Vinogradova, L. V. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1982, vol. 31, # 5, p. 987 - 990][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1982, # 5, p. 1107 - 1112]

17
[ 64-17-5 ]
[ 108-94-1 ]
[ 141-28-6 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 7944 - 7948
[2]Bulletin of the Chemical Society of Japan,1989,vol. 62,p. 2399 - 2400

18
[ 34683-73-3 ]
[ 141-28-6 ]
[ 198995-68-5 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 14807 - 14820

19
[ 141-28-6 ]
[ 925-90-6 ]
[ 207298-22-4 ]

Reference： [1]Russian Journal of Organic Chemistry,1997,vol. 33,p. 830 - 834
Zhurnal Organicheskoi Khimii,1997,vol. 33,p. 898 - 901
[2]Tetrahedron Letters,2010,vol. 51,p. 3497 - 3500

20
[ 4706-43-8 ]
[ 141-28-6 ]
1,8-bis-benzotriazol-1-yl-1,8-diphenyl-octane-2,7-dione [ No CAS ]

Reference： [1]Heterocycles,1998,vol. 48,p. 1567 - 1574

21
[ 1070-34-4 ]
[ 7732-18-5 ]
potassium persulfate [ No CAS ]
[ 141-28-6 ]
[ 105-37-3 ]
[ 140-88-5 ]

Reference： [1]Helvetica Chimica Acta,1936,vol. 19,p. 152

22
[ 141-28-6 ]
[ 1519-39-7 ]
[ 659726-13-3 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 297 - 299

23
[ 141-28-6 ]
[ 6089-04-9 ]
[ 371918-06-8 ]

Reference： [1]New Journal of Chemistry,2001,vol. 25,p. 912 - 916

24
[ 141-28-6 ]
[ 7149-18-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1901,vol. 317,p. 104

25
[ 141-28-6 ]
[ 108250-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In benzene;	EXAMPLE 40 4-[6-(p-Chlorophenyl)hexanamido]benzoic acid To a solution of 101 g. of ethyl adipate in 500 ml. of benzene is slowly added 120 ml. of thionylchloride. The mixture is refluxed for 4.5 hours, cooled, and evaporated. The residue is evaporated three times from 500 ml. of benzene, giving 113 g. of ethyl adipoyl chloride as a yellow liquid.

Reference： [1]Patent: US4536346,1985,A

26
[ 124-04-9 ]
2-ethoxycarbonyloxyimino-2-cyanoacetic acid amide [ No CAS ]
[ 141-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran;	EXAMPLE D To a solution of adipic acid (1.46 g) and triethylamine (2.8 ml) in tetrahydrofuran (30 ml), 2-ethoxycarbonyloxyimino-2-cyanoacetic acid amide (3.7 g) is added, and the resulting mixture is stirred at room temperature for 2 hours. The reaction mixture is treated as in Example A to give diethyl adipate (1.5 g) as an oil. IR absorption spectrum: 1730 cm-1 (carbonyl of the ester)

Reference： [1]Patent: US3976635,1976,A

28
[ 627-93-0 ]
[ 64-17-5 ]
[ 627-91-8 ]
[ 141-28-6 ]
[ 18891-13-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 11.2% 2: 40.5% 3: 43.5%	With water; hydrogen In methanol

Reference： [1]Jiang, Hong-Bin; Jiang, Hai-Jun; Su, Ke; Zhu, De-Ming; Zheng, Xue-Li; Fu, Hai-Yan; Chen, Hua; Li, Rui-Xiang [Applied Catalysis A: General, 2012, vol. 447-448, p. 164 - 170]

29
[ 53007-35-5 ]
[ 141-28-6 ]

Reference： [1]Synlett,2013,vol. 24,p. 1391 - 1394

30
[ 141-28-6 ]
[ 71-36-3 ]
[ 105-99-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid at 105 - 115℃; Dean-Stark; Microwave irradiation;

Reference： [1]Bowman, Matthew D.; Holcomb, Jennifer L.; Kormos, Chad M.; Leadbeater, Nicholas E.; Williams, Victoria A. [Organic Process Research and Development, 2008, vol. 12, # 1, p. 41 - 57]

31
[ 141-28-6 ]
[ 100-44-7 ]
[ 243139-32-4 ]

Yield	Reaction Conditions	Operation in experiment
95.4%	With sodium ethanolate; In tetrahydrofuran; at 60 - 65℃; for 58.58h;Large scale;	Example 1 Synthesis of diethyl-2,5-dibenzylhexanedioic acid In a 20 L jacketed reactor, NaOEt (632 g) was suspended in 5200 mL THF and heated to 60 C. Diethyl hexanedioic acid (1520 g) was added slowly, maintaining an internal temperature?65 C. The approximate addition time was 50 min. The mixture was stirred for 16 h at 60 C. Benzyl chloride (1066 g) was added over 3.75 h. The mixture was stirred at 60 C. for 3.5 h then cooled to 22 C. Additional NaOEt (635 g) was added over 2 h, heated to 60 C., and stirred for 16 h. Benzyl chloride (1143 g) was added over 1.75 h. The mixture was heated to 65 C. for 6 h and then cooled to 30 C. NaOEt (130 g) was added and the mixture heated to 60 C. for 5 h to convert the ring closed cyclopentanone intermediate to the desired open chain form. Benzyl chloride (269 g) was added over 1.75 h and the mixture stirred at 60 C. for 2 h to convert any unreacted NaOEt to benzyl ethyl ether. Ethanol (291 g) was added and the mixture was cooled to 25 C. To the solution was added 4775 mL of 0.01 M HCl to neutralize the bases. Toluene (4 L) was added, the organic layer was collected, and the organic liquid was concentrated. The resulting oil (3361 g, 95.4%) was further dried with a N2 sweep to remove volatiles. The equilibrium mixture of stereoisomers was characterized by 1H NMR, 13C NMR, and MS. 1H NMR (300 MHz, CDCl3) delta 7.30-7.13 (m, 10H), 4.08-3.98 (m, 4H), 2.97-2.88 (m, 2H), 2.77-2.60 (m, 4H), 1.75-1.62 (m, 2H), 1.57-1.46 (m, 2H), 1.36-1.23 1.13 (ap t, J=7.1 Hz, 6H); 13C NMR (75 MHz, CDCl3) delta 175.0, 139.0, 128.8, 128.2, 162.2, 60.1, 47.1, 38.3, 29.3, 14.1; EI MS m/z 382 (M)+.

Reference： [1]Patent: US2014/51888,2014,A1 .Location in patent: Paragraph 0115-0117

32
[ 141-28-6 ]
[ 74-88-4 ]
[ 19781-07-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With magnesium; In diethyl ether; at 25℃; for 48h;Inert atmosphere;	General procedure: GaldenHT135/200 = 1:1 (2 mL) was placed in a test tube(13 mm Phi × 105 mm), to which MeI (571 mg, 4.0 mmol) wasadded slowly using a glass pipette under argon. Anhydrous Et2O(1 mL) was added slowly, whereupon three layers formed. Mgpowder (98 mg, 4.0 mmol) was then added slowly, and floatedbetween the Galden and ether layers, whereupon four layersformed. Subsequently, a solution of 2-decanone (1a, 313 mg, 2.0mmol) in anhydrous Et2O (3 mL) was added to the ether layer.The bottom layer was stirred slowly at 25 C for 2 d, taking carenot to mix the four layers. The ether solution and Mg salt weretaken into a flask, to which hydrochloric acid (2 M) was addedto quench the reaction, while cooling in an ice bath. The organiclayer was separated, and the aqueous layer was extracted withEt2O. The organic layer was collected, dried over Na2SO4, andconcentrated. The residue was purified by column chromatographyon silica gel (hexane-Et2O, 3:1) to give 2-methyl-2-decanol (2a)

Reference： [1]Synlett,2015,vol. 26,p. 1276 - 1280

33
[ 7149-59-9 ]
[ 141-28-6 ]

Yield	Reaction Conditions	Operation in experiment
> 90%	With ruthenium-carbon composite; hydrogen; In ethanol; at 250℃; under 77574.3 Torr; for 4h;Autoclave;	Example 21 Hydrogenation of Diethyl-3-Ketoadipate to Diethyladipate 300 Ml of a 30 wt % solution of diethyl-3-ketoadipate in ethanol is added to a 500 ml autoclave containing 5 g of Ru/C catalyst. The reactor is heated to 250 C. under 1500 psi of hydrogen and maintained at temperature and pressure for 4 hours. At the end of the reaction, the vessel is cooled and diethyladipate is recovered in >90% yield by distillation.

Reference： [1]Patent: US2015/225329,2015,A1 .Location in patent: Paragraph 0138

34
[ 78-39-7 ]
[ 107-18-6 ]
[ 109-94-4 ]
[ 141-28-6 ]

Yield	Reaction Conditions	Operation in experiment
84%		In an oven-dried 20 mL autoclave, 7.5 mmol triethylorthoacetate (1.218 g,2 eq.) and 3.75 mmol allyl alcohol (0.218 g, 1 eq.) were weighed under air.Afterwards, the autoclave was sealed and placed in the preheated oil bath andallowed to stir for 16 h at 150Cat ~ 750 rpm. After that, the autoclave was cooled down to 0C by using a water-ice bathand carefully opened. Formic acid (136 mg, 2.95 mmol, 1 eq.) was added and thereactor was closed again, and allowed to stir in an oil bath at 100C for 3 h at ~ 750rpm. Meanwhile, the Pd-catalytic system was prepared by adding Pd(acac)2(5.6 mg, 0.019 mmol, 0.5 mol%) and the ligand 1,2-DTBPMB (29.0 mg, 0.075 mmol,2 mol%) to an oven-dried Schlenk-tube in an Argon counter stream. Ethanol (0.3mL, 4.9 mmol, 1.3 eq. in case of ethyl formate addition, 0.75 mL, 12.0 mmol,3.2 eq. in case of omitted ethyl formate addition) and ethyl formate (5) (0.7 mL, 8.7 mmol, 2.3 eq., only incase of tandem reaction) were added and the solution was homogenized by simpleshaking. Methanesulfonic acid (28.7 mg, 0.30 mmol, 8 mol%) was added and afterthat, the reactor was cooled down to 0C by using a water-ice bath and carefullyopened. The catalyst mixture was transferred to the autoclave by syringe in anargon counter stream. The autoclave was put in the preheated oil bath at 100C and stirred for 20 h at~ 750 rpm. The autoclave was cooled down to room temperature, using a water-ice bath, and the reaction mixture was taken from theopened autoclave, transferred to a 6 mL glass vial for storing purposes and analiquot was taken for quantitative GC-analysis, according to the generalinformation. In case of preparative isolation of the product, the reactionmixture was diluted with diethyl ether, transferred to a 100 mL round bottomflask and the autoclave was rinsed with diethyl ether. The combined organicphases were washed subsequently with 10% HCl, sat. NaHCO3 solutionand brine and dried over Na2SO4. The solution wasconcentrated using a rotary evaporator and purified by flash columnchromatography using c-hexane/ethylacetate (4:1, Rf = 0.34) to yield diethyl adipate in 84% as acolorless liquid.

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 371 - 374

35
[ 1968-40-7 ]
[ 109-94-4 ]
[ 141-28-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With palladium(II) acetylacetonate; methanesulfonic acid; 1,2-bis[di(t-butyl)phosphinomethyl]benzene; In ethanol; at 100℃; for 20h;Inert atmosphere; Autoclave;	In an oven-dried Schlenk-tube, Pd(acac)2(5.6 mg, 0.019 mmol, 0.5 mol%) and the ligand 1,2-DTBPMB (29.0 mg, 0.075 mmol,2 mol%) were added in an Argon counter stream. Ethanol (0.75 mL, 12.0 mmol, 3.2eq.) and ethyl formate (5) (0.7 mL,8.7 mmol, 2.3 eq.) were added and the solution was homogenized by simpleshaking. Afterwards, the substrate ethyl 4-pentenoate (4) (480 mg, 3.75 mmol, 1 eq.) and methanesulfonic acid(28.7 mg, 0.30 mmol, 8 mol%) were added and the reaction mixture wastransferred to the custom made 20 mL oven-dried autoclave by syringe in anargon counter stream. After that, the autoclave was placed in the preheated oilbath and allowed to stir for 20 h at 100C at ~ 750 rpm. The autoclave was cooleddown to room temperature, using a water-ice bath, and the reaction mixture wastaken from the opened autoclave, transferred to a 6 mL glass vial for storingpurposes and an aliquot was taken for quantitative GC-analysis, according tothe general information.Incase of preparative isolation of the product, the reaction mixture was dilutedwith ethyl acetate and washed with sat. NaHCO3 solution and brineand dried over Na2SO4. The product mixture was concentratedusing a rotary evaporator and the clear product was purified by flash columnchromatography using c-hexane/ethylacetate (4:1, Rf = 0.34) to yield diethyl adipate (6) in 91% as a colorless liquid. The spectroscopic data were in accordance withexamples from the literature and an authentic commercial sample(Sigma-Aldrich).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 371 - 374

36
[ 64-17-5 ]
[ 74-85-1 ]
[ 3588-17-8 ]
[ 141-28-6 ]
[ 72903-27-6 ]
[ 636-09-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethanol; ethene; trans,trans-muconic acid With dodecatungstosilic acid at 200℃; for 6h; Autoclave; Stage #2: With 10 mol% palladium on carbon at 200℃; for 6h; Autoclave; Inert atmosphere;

Reference： [1]Lu, Rui; Lu, Fang; Chen, Jiazhi; Yu, Weiqiang; Huang, Qianqian; Zhang, Junjie; Xu, Jie [Angewandte Chemie - International Edition, 2016, vol. 55, # 1, p. 249 - 253][Angew. Chem., 2016, vol. 128, # 1, p. 257 - 261,5]

37
[ 141-28-6 ]
[ 623-51-8 ]
C₁₁H₁₅NO₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.3%		dihydrothiophen-4-one (III, R is ethyl)A 2-liter four-necked flask equipped with a stirrer, thermometer and dropping funnel was charged with 400 g of ethanol, 202.2 g (1.0 mol) of <strong>[141-28-6]diethyl adipate</strong>, 255 g of fresh 28% sodium ethoxide in ethanol and cooled to -10C , 61.0 g (1.0 mol) of nitromethane was added dropwise at an internal temperature of -5 to 0 C for about 2 hours, and the reaction was completed at 10 to 15 C for 4 hours. The resulting reaction liquid was then added dropwise to a mixture of 126.2 g (1.05 mol) of ethyl mercaptoacetate and 78 g of acetic acid, and the dropping was maintained at 40-45 C for about 2 hours. The reaction mixture was heated to 50-55 C 3 hours. 300 g of toluene was added and the layers were separated. The aqueous layer was extracted three times with toluene, 150 g of toluene each time, the combined toluene phase, and 60 g of saturated chlorinated water. The reaction mixture was cooled to & lt; The organic phase was dried over anhydrous sodium sulphate (20 g) for 4 hours and the toluene removed to give 2-ethoxycarbonyl-n-butyl-3-nitro-4,5-dihydrothiophene- 4-one 216.5 g, liquid purity 98.1%, yield 79.3%.

Reference： [1]Patent: CN104447791,2016,B .Location in patent: Paragraph 0046; 0047

38
[ 57042-08-7 ]
[ 201230-82-2 ]
[ 141-28-6 ]
diethyl 3-formylhexanedioate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 2257 - 2262

39
[ 141-28-6 ]
[ 24569-89-9 ]
diethyl 2-(adamantan-1-yl)adipate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In diethyl ether; at 90 - 110℃; for 6h;	General procedure: From a mixture of 10 g (0.058 mol) of diethyl succinate 2a and a solution of 2 g (0.015 mol) of propellane 1 in anhydrous ethyl ether the solvent was distilled off, the residue was heated for 6 h at 90-110. Excess ester 2a was distilled off at a reduced pressure, the residue was distilled in a vacuum.

Reference： [1]Russian Journal of Organic Chemistry,2017,vol. 53,p. 160 - 162
Zh. Org. Khim.,2017,vol. 53,p. 174 - 176,3

40
[ 64-17-5 ]
[ 6117-91-5 ]
[ 201230-82-2 ]
[ 51251-11-7 ]
[ 141-28-6 ]
[ 18545-83-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; palladium(II) acetylacetonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In diethyl ether; toluene; at 105℃; under 30003 Torr; for 24h;Autoclave; Inert atmosphere;	A 4 ml glass vial is charged with [Pd(acac)2] (3.77 mg, 1 mol %), Xantphos (8.8 mg, 1.5 mol %) and a magnetic stirrer. This vial is closed with a phenolic resin cap consisting of a septum made from Teflon-coated styrene-butadiene rubber. This septum is pierced with a cannula, and the atmosphere in the vial is replaced by an argon atmosphere through this cannula by three cycles of application of reduced pressure and purging with argon. Through this cannula, 2 ml of toluene, crotyl alcohol (87 mul, 1 mmol), ethanol (175 mul, 3 mmol) and 1 M hydrochloric acid solution in diethyl ether (50 mul, 5 mol %) are then injected by means of syringes. This vial is then placed in a metal plate which is then transferred into a 300 ml steel autoclave from Parr Instruments under an argon atmosphere. After the autoclave has been purged three times with CO, CO is injected to 40 bar at room temperature. The reaction is conducted while stirring with a magnetic stirrer at 105 C. for 24 hours. After the end of the reaction, the autoclave is cooled down and the pressure is released gradually. The autoclave is purged three times with nitrogen. Subsequently, isooctane (100 mul) is added as internal standard. The yield and selectivity are determined by means of GC analysis.

Reference： [1]Patent: US2017/174610,2017,A1 .Location in patent: Paragraph 0055; 0056; 0057

41
[ 598-32-3 ]
[ 64-17-5 ]
[ 201230-82-2 ]
[ 51251-11-7 ]
[ 141-28-6 ]
[ 18545-83-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; palladium(II) acetylacetonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In diethyl ether; toluene; at 105℃; under 30003 Torr; for 24h;Inert atmosphere; Autoclave;	A 4 ml glass vial is charged with [Pd(acac)2] (3.77 mg, 1 mol %), Xantphos (8.8 mg, 1.5 mol %) and a magnetic stirrer. This vial is closed with a phenolic resin cap consisting of a septum made from Teflon-coated styrene-butadiene rubber. This septum is pierced with a cannula, and the atmosphere in the vial is replaced by an argon atmosphere through this cannula by three cycles of application of reduced pressure and purging with argon. Through this cannula, 2 ml of toluene, but-3-en-2-ol (87 mul, 1 mmol), ethanol (175 mul, 3 mmol) and 1 M hydrochloric acid solution in diethyl ether (50 mul, 5 mol %) are then injected by means of syringes. This vial is then placed in a metal plate which is then transferred into a 300 ml steel autoclave from Parr Instruments under an argon atmosphere. After the autoclave has been purged three times with CO, CO is injected to 40 bar at room temperature. The reaction is conducted while stirring with a magnetic stirrer at 105 C. for 24 hours. After the end of the reaction, the autoclave is cooled down and the pressure is released gradually. The autoclave is purged three times with nitrogen. Subsequently, isooctane (100 mul) is added as internal standard. The yield and selectivity are determined by means of GC analysis.

Reference： [1]Patent: US2017/174610,2017,A1 .Location in patent: Paragraph 0055; 0058; 0059

42
[ 64-17-5 ]
[ 261900-70-3 ]
[ 141-28-6 ]
ethyl (S)-2-hydroxy-2-((R)-5-oxotetrahydrofuran-2-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		The headspace above a solution of 1 (132 mg), MTO (15 mg), and 10% Pd/C (15 mg) in EtOH (7.5 mL) in a Parr reactor was purged with H2 and maintained under 1 atm of H2. The reaction was heated to 150C. After 1.5 hours, the reaction was cooled to room temperature and the reactor was pressurized to 300 psi with H2. The reaction was re-heated to 150C for 1.5 hours. The reaction was cooled to room temperature. The headspace was purged with N2 to facilitate removal of residual H2. The headspace was then purged with 1 atm 02, capped, and stirred at room temperature overnight. The reaction was purged with N2 to remove residual 02. The process described above (i.e., heating at 1 atm H2, heating at 300 psi H2, followed by 02 treatment) was repeated 3 times

Reference： [1]Patent: WO2017/147098,2017,A1 .Location in patent: Paragraph 0122; 0123; 0124
[2]Journal of the American Chemical Society,2017,vol. 139,p. 14001 - 14004

43
[ 45214-05-9 ]
[ 141-28-6 ]
ethyl (S)-2-hydroxy-2-((R)-5-oxotetrahydrofuran-2-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Based upon the synthetic route above, the similarity of the reaction conditions facilitated a one-pot sequence for the chemical transformation of diethyl glucarate to diethyl adipate. Palladium and rhenium catalysts added at various times during the reaction course led to complicated reaction mixtures. It was found, however, that modulation of the H2 pressure combined with one additional loading of rhenium (i.e. MTO), provided diethyl adipate in 72% overall yield (NMR yield) (see FIG. 8). The overall yield was likely 10-15% higher due to the repetitive removal of reaction aliquots for reaction monitoring. The one-pot sequence was made possible with the finding that an increase in H2 pressure following the completion of DODH reactivity enabled olefin hydrogenation to occur (seeFIG. 9)

Reference： [1]Patent: WO2017/147098,2017,A1 .Location in patent: Paragraph 0111
[2]Patent: WO2017/147098,2017,A1

44
[ 21959-75-1 ]
[ 141-28-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With palladium 10% on activated carbon; hydrogen; In ethanol; under 760.051 Torr;	A solution of 4 (68 mg) and 10% Pd/C (5 mg) in EtOH (2 mL) stirred under 1 atm of H2 (balloon) overnight. The reaction was filtered through celite, rinsed with DCM, and concentrated to provide 5 (63 mg, 97%) as a colorless oil

Reference： [1]ChemCatChem,2018,vol. 10,p. 3419 - 3423
[2]Patent: WO2017/147098,2017,A1 .Location in patent: Paragraph 0110; 0111; 0152; 0156

45
[ 64-17-5 ]
[ 261900-70-3 ]
[ 141-28-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium perrhenate; phosphoric acid; palladium 10% on activated carbon; hydrogen; at 150℃; under 3878.71 Torr; for 72h;	A Parr reactor charged with polyol (7.5 mmol), KReO4 (22 mg), 10% Pd/C (60 mg), 85% H3P04 (26 mg), and EtOH (7.5 mL) was pressurized to 75 psi with H2. The reaction was placed in a preheated oil bath set to 150C for a 4 hours. The reaction mixture was cooled to room temperature, filtered, rinsed with ethanol, and concentrated.Mesitylene was added to the crude residue as a standard for the determination of yields by NMR

Reference： [1]Patent: WO2017/147098,2017,A1 .Location in patent: Paragraph 0130; 0132; 0133; 0142; 0143

46
[ 503-74-2 ]
[ 1070-34-4 ]
[ 592-13-2 ]
[ 10236-10-9 ]
[ 141-28-6 ]

Reference： [1]Green Chemistry,2019,vol. 21,p. 2334 - 2344

47
[ 141-28-6 ]
[ 106-94-5 ]
[ 7179-24-0 ]

Yield	Reaction Conditions	Operation in experiment
155 g		107 mg of magnesium was added to a three-necked flask with an internal volume of 5 L equipped with a ball plug, a cooling tube, a dropping funnel and a three-way cock, and well dried. After nitrogen substitution, 300 mL of dry tetrahydrofuran (THF) was added to the extent that the surface of magnesium was hidden, and then 20 mL of propyl bromide was added to confirm the start of the Grignard reaction.After adding 1,700 mL of THF, 364 mL of propyl bromide was added dropwise at such a rate as to gently reflux.After completion of the dropwise addition, the reaction solution was stirred overnight while refluxing.The reaction solution was cooled to room temperature using a water bath, and 133 mL of <strong>[141-28-6]diethyl adipate</strong> synthesized in Production Example 1 was added dropwise over 1 hour.After completion of the dropwise addition, the reaction solution was stirred overnight while refluxing.After completion of the reaction, the reaction solution was cooled using an ice bath, and then 200 mL of ammonium chloride was added and stirred well until a solid was formed in the reaction solution.The solid was separated by suction filtration, 2,000 mL of 1N hydrochloric acid was added to the obtained organic layer to separate it into an aqueous layer and an organic layer, and the aqueous layer was extracted twice with 1,000 mL of ether.The obtained organic layers were combined, and saturated aqueous sodium hydrogen carbonate solution 2,000The organic layer was washed with 0 mL and 2,000 mL of saturated brine and dried over sodium sulfate.Subsequently, the organic solvent was distilled off to obtain 155 g of 4,9-dipropyldodecane-4,9-diol.In addition, 4,9-dipropyldodecane-4,9-diol was identified by NMR analysis.
155 g		107 g of magnesium was added to a three-necked flask with an internal volume of 5 L equipped with a ball plug, a cooling tube, a dropping funnel and a three-way cock and dried well.After substituting with nitrogen, 300 mL of dried tetrahydrofuran (THF) was added until the surface of the magnesium was hidden, and then 20 mL of propyl bromide was added to confirm the start of the Grignard reaction.After adding 1,700 mL of THF, 364 mL of propyl bromide was added dropwise at such a rate as to gently reflux.After completion of the dropwise addition, the reaction solution was stirred overnight while refluxing. *The reaction solution was cooled to room temperature using a water bath, and 133 mL of <strong>[141-28-6]diethyl adipate</strong> synthesized in Production Example 1 was added dropwise over 1 hour.After completion of the dropwise addition, the reaction solution was stirred overnight while refluxing.After completion of the reaction, the reaction solution was cooled using an ice bath, and then 200 mL of ammonium chloride was added and stirred well until a solid was formed in the reaction solution.The solid was separated by suction filtration, 2,000 mL of 1N hydrochloric acid was added to the obtained organic layer to separate it into an aqueous layer and an organic layer, and the aqueous layer was extracted twice with 1,000 mL of ether.The obtained organic layers were combined, washed with 2,000 mL of saturated aqueous sodium hydrogen carbonate solution and 2,000 mL of saturated brine, and the organic layer was dried over sodium sulfate.Subsequently, the organic solvent was distilled off to obtain 155 g of 4,9-dipropyldodecane-4,9-diol. In addition, 4,9-dipropyldodecane-4,9-diol was identified by NMR analysis.

Reference： [1]Patent: JP2019/142782,2019,A .Location in patent: Paragraph 0040; 0041
[2]Patent: JP2019/142783,2019,A .Location in patent: Paragraph 0056; 0057

48
[ 64-17-5 ]
[ 201230-82-2 ]
[ 106-99-0 ]
[ 141-28-6 ]

Reference： [1]Science,2019,vol. 366,p. 1514 - 1517

49
[ 124-04-9 ]
[ 141-28-6 ]

Yield	Reaction Conditions	Operation in experiment
1988 g	With ethanol; toluene-4-sulfonic acid; at 78℃; for 8h;Large scale;	To 10L, adipic acid (1461 g) was added, ethanol (4.5L) was added, p-toluenesulfonic acid (34.4g) was added, and then heated to 78 C, and reacted 8 hours to give a reacted solution. The reacted solution was subjected to reduced pressure distillation to remove ethanol, and the reaction solution was collected at 1.73 kPa pressure for a fraction of 124 C - 130 C to yield diethyl adipate (datdatdatin) as a colorless oily liquid product 1988 g.

Reference： [1]Patent: CN111187166,2020,A .Location in patent: Paragraph 0050-0054; 0066-0069; 0072-0075

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P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 141-28-6 ] {[proInfo.proName]}

Quality Control of [ 141-28-6 ]

Related Doc. of [ 141-28-6 ]

Product Details of [ 141-28-6 ]

Calculated chemistry of [ 141-28-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 141-28-6 ]

Application In Synthesis of [ 141-28-6 ]

[ 141-28-6 ] Synthesis Path-Upstream 1~4

[ 141-28-6 ] Synthesis Path-Downstream 1~49

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry