35354-29-1|3,5-Diacetoxybenzoic acid| Ambeed

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Quality Control of [ 35354-29-1 ] Purity: 98% SDS Specification

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Product Details of [ 35354-29-1 ]

CAS No. :	35354-29-1
Formula :	C₁₁H₁₀O₆
M.W :	238.19
SMILES Code :	O=C(O)C1=CC(OC(C)=O)=CC(OC(C)=O)=C1
MDL No. :	MFCD00017591
InChI Key :	QBTDQJMLMVEUTQ-UHFFFAOYSA-N
Pubchem ID :	539869

Safety of [ 35354-29-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Application In Synthesis of [ 35354-29-1 ]

* 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.

Downstream synthetic route of [ 35354-29-1 ]

[ 35354-29-1 ] Synthesis Path-Downstream 1~35

1
[ 35354-29-1 ]
[ 39192-49-9 ]

Yield	Reaction Conditions	Operation in experiment
98.2%	With thionyl chloride; In dichloromethane;Reflux;	Step 2: Diacetoxybenzoyl Chloride A 250 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 15.4 g (64.7 mmol) of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong>, 10 ml of thionyl chloride and 80 ml of CH2Cl2. The mixture was refluxed for 3-5 hours. Then the solvent and remaining thionyl chloride were distilled off. Fresh CH2Cl2 was added and distilled off again. The crude solid was dissolved in 120 ml toluene, and the solution was filtered. Evaporated the solvent out and dried the product at room temperature under 1 mbar. 16.3 g of 3,5-diacetoxybenzoyl chloride were obtained as a white solid. The yield was 98.2%.
98.2%	With thionyl chloride; In dichloromethane;Reflux;	Step 2: Diacetoxybenzoyl chloride A 250 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 15.4 g (64.7 mmol) of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong>, 10 ml of thionyl chloride and 80 ml of CH2Cl2. The mixture was refluxed for 3 to 5 hours. Then the solvent and remaining thionyl chloride were distilled off. Fresh CH2Cl2 was added and distilled off again. The crude solid was dissolved in 120 ml toluene, and the solution was filtered. Evaporated the solvent out and dried the product at room temperature under 1 mbar. 16.3 g of 3,5-diacetoxybenzoyl chloride were obtained as a white solid. The yield was 98.2 %.
95.5%	With thionyl chloride;N,N-dimethyl-formamide; In toluene; at 20 - 80℃; for 2.25h;	6. Preparation of 3,5-diacetoxybenzoyl chloride To a mixture of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> (8.00 g, 33.59 mmol) and dimethylformamide (5 drops) in toluene was added freshly distilled thionylchloride (16 mL). The mixture was stirred for 15 min under nitrogen atmosphere at ambient temperature. Then it was refluxed for 2 h at 80 C. in a hot water bath. The excess thionyl chloride was evaporated in vacuo and toluene was added. Insoluble yellow solid was discarded. Toluene was evaporated in vacuo and gave 3,5-diacetoxybenzoyl chloride (8.23 g, 95.5%), which can be recrystallized from hexane. Data are: 1H NMR (CDCl3, 300 MHz) δ 7.75 (d, 2H), 7.29 (t, 1H), 2.34 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 168.8, 167.0, 151.4, 135.3, 122.8, 122.0, 21.2; mp=89.5-91 C.; HRMS (EI+) found 256.0130 M+, calcd 256.0139 for C11H9O5Cl; Anal. Calcd for C11H9O5Cl: C, 51.48; H, 3.53. Found: C, 51.60; H, 3.68.

	In thionyl chloride;	The obtained <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> (2.38 g, 10 mM) was dissolved in 5 ml of SOCl2 and the solution was heated under reflux at 80 C. for 1 hour. The solvent SOCl2 was distilled off under reduced pressure to yield 3,5-diacetoxybenzoyl chloride (2.44 g).
	With thionyl chloride; In benzene;	42 g of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> are heated under reflux for 5 hours with 300 ml of benzene and 26 ml of thionyl chloride. The reaction mixture is concentrated by evaporation and the residue is taken up in benzene and again concentrated by evaporation. 3,5-diacetoxybenzoyl chloride having a melting point of 85-87 is thus obtained. In a manner analogous to that described in Example 1, 1-[2-(4-chlorophenyl)-ethyl]-4-(3,5-diacetoxybenzoyl)-piperazine hydrochloride having a melting point of 220 (decomposition) is obtained from 3,5-diacetoxybenzoyl chloride.
	With thionyl chloride; In N,N-dimethyl-formamide; toluene; at 100℃; for 3h;Inert atmosphere;	A suspension of <strong>[35354-29-1]3,5-diacetoxybenzoic acid</strong> (8.022 g, 33.71 mmol) in a mixture of toluene (130 mL),DMF (500 μL) and thionyl chloride (16.00 mL, 220.6 mmol) was heated at 100 C for three hours underan argon gas atmosphere. The solvents were removed by vacuum distillation and the residue re-suspendedin toluene (85 mL) and sonicated under vacuum to remove dissolved gases. 4-Acetoxystyrene (5.74 mL,37.5 mmol), N-ethylmorpholine (4.31 mL, 33.9 mmol) and palladium diacetate (35 mg, 0.16 mmol,0.46 mol %) were added and the reaction heated to reflux for 2 h. Further palladium diacetate (116 mg,0.52 mmol, 1.54 mol %) was added and the reaction left to reflux overnight. On return to roomtemperature, ethyl acetate (500 mL) was added, the solution washed with 0.1 M aq. HCl (2 × 300 mL)and water (300 mL) and then dried and evaporated to return a brown solid. Purification with columnchromatography (isocratically eluted with 2:1 Et2O/hexane) gave 7.888 g of a white solid, shown by1H-NMR spectroscopy to be predominantly the desired adduct. Further chromatography (gradienteluted starting with 4:1 hexane/EtOAc and finishing with 2:1 hexane/EtOAc) returned pure (E)-3,4′,5-triacetoxystilbene (6.071 g, 51%) as a white solid.
	With thionyl chloride; at 78℃; for 4h;	General procedure: 3,4,5-triacetoxybenzoic acid 4a (2000 mg, 6.756 mmol) wasdissolved in SOCl2 (8000 mg, 67.244 mmol). The solution was thenheated under reflux at 78 C for 4 h. The solvent was removed usinga rotary evaporator under reduced pressure to yield white solid.Yielding 99% compound 5a (2100 mg) as a white solid. Compounds5b-c and 7a were synthesized following the procedure of preparation5a.

References: [1]Patent: US2012/22284,2012,A1 .Location in patent: Page/Page column 2.
[2]Patent: EP2404891,2012,A1 .Location in patent: Page/Page column 4.
[3]Tetrahedron Letters,2006,vol. 47,p. 5811 - 5814.
[4]Patent: US2008/255382,2008,A1 .Location in patent: Page/Page column 25.
[5]Tetrahedron Letters,2003,vol. 44,p. 4819 - 4822.
[6]Chemische Berichte,1941,vol. 74,p. 869,872.
[7]Zhurnal Obshchei Khimii,1938,vol. 8,p. 1399,1412-1421.
Chemisches Zentralblatt,1939,vol. 110,p. 4212.
[8]Journal of the American Chemical Society,1992,vol. 114,p. 3346 - 3355.
[9]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 725 - 733.
[10]Journal of Medicinal Chemistry,1998,vol. 41,p. 4790 - 4799.
[11]Journal of the Indian Chemical Society,1998,vol. 75,p. 810 - 822.
[12]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 1402 - 1407.
[13]Patent: US5661153,1997,A .
[14]Patent: US4804661,1989,A .
[15]Molecules,2015,vol. 20,p. 17601 - 17613.
[16]European Journal of Medicinal Chemistry,2019,vol. 179,p. 233 - 245.

2
[ 99-10-5 ]
[ 108-24-7 ]
[ 35354-29-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; at 90 - 100℃; for 0.166667h;	A mixture of 7.7 g (0.05 mol) of 3,5-dihydroxybenzoic acid (1), 25 mL of acetic anhydride and 2 mL of triethylamine was mixed and stirred for 10 min and heated at 90 to 100 C. TLC was monitored. Product into the ice water, a large number of white precipitate generated, filtered to obtain a white solid is the crude product,Recrystallization from ethanol gave 11.0 g of white crystals (2) in 92% yield.
91%	at 130℃; for 4h;	General procedure: Garlic acid (2000 mg, 11.763 mmol) was dissolved in acetic anhydride(7205 mg, 70.578 mmol). The solution was then heatedunder reflux at 130 C for 4 h, after which the deionized water(4 ml) was add to the solution to remove the unreacted acetic anhydride.The solvent was removed using a rotary evaporator underreduced pressure to yield white solid. The product was recrystallizedin CH2Cl2 and dried under vacuum. Yielding 95% compound 4a(3308 mg) as a white solid. Compounds 4b-c were synthesizedfollowing the procedure of preparation 4a.
90%		Preparation of 3,5-diacetyloxybezoic acid: Reaction Scheme 1-iTo 200 ml of tetrahydrofuran, 15.4 g (0.09 mol) of 3,5-dihydroxybenzoic acid and 38 ml (0.27 mol) of triethylamine were added, and the reaction mixture was stirred for 10 minutes. To the reaction mixture, 23 ml (0.24 mol) of acetic anhydride was added dropwise, and then the resultant mixture was refluxed for 3 hours. The reaction mixture was cooled to room temperature and allowed to evaporate under reduced pressure. Then, dichloromethane and water were added thereto, and the organic layer was washed with water and 1N aqueous HCl solution many times, and allowed to evaporate under reduced pressure. Hexane was added to the remaining oil to form precipitate. The precipitate was filtered under reduced pressure to obtain 15 g (90%) of the target product.

90%		[Example 1] Preparation of 3,5-dihydroxy-N-(4-hydroxyphenyl)benzamide; Preparation of 3,5-diacetyloxybezoic acid:; Reaction Scheme l-i>To 200ml of tetrahydrofuran, 15.4g (0.09mol) of 3,5-dihydroxybenzoic acid and 38ml (0.27mol) of triethylamine were added, and the reaction mixture was stirred for 10 minutes. To the reaction mixture, 23ml (0.24mol) of acetic anhydride was added dropwise, and then the resultant mixture was refluxed for 3 hours. The reaction mixture was cooled to room temperature and allowed to evaporate under reduced pressure. Then, dichloromethane and water were added thereto, and the organic layer was washed with water and IN aqueous HCl solution many times, and allowed to evaporate under reduced pressure. Hexane was added to the remaining oil to form precipitate. The precipitate was filtered under reduced pressure to obtain 15g (90%) of the target product.
88.4%	With pyridine; at 100℃;	Step 1: Acetoxybenzoic Acid A 100 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 30 g (0.195 mol) of 3,5-dihydroxybenzoic acid, 47 ml (0.497 mol) of acetic anhydride and 2.4 ml (29.8 mmol) of pyridine. The mixture was heated to 100 C. and kept under stirring for 3-4 hours then cooled down, poured into 400 ml of ice water and filtered. The filter cake was washed with ice water and dried at 45 C. under 1 mbar vacuum. 41 g of 3,5-diacetoxybenzoic acid as a white solid was obtained. The yield was 88.4%.
88.4%	With pyridine; at 100℃;	Step 1: Acetoxybenzoic acid A 100 ml three-necked flask with magnetic stirrer, thermometer and condenser was charged with 30 g (0.195 mol) of 3,5-dihydroxybenzoic acid, 47ml (0.497 mol) of acetic anhydride and 2.4 ml (29.8 mmol) of pyridine. The mixture was heated to 100 C and kept under stirring for 3 to 4 hours then cooled down, poured into 400 ml of ice water and filtered. The filter cake was washed with ice water and dried at 45 C under 1 mbar vacuum. 41 g of 3,5-diacetoxybenzoic acid as a white solid was obtained. The yield was 88.4 %.
72%	With pyridine; dmap; In ethyl acetate; at 0 - 20℃;	A suspension of 3,5-dihydroxybenzoic acid (15.40 g, 0.100 mol) in ethyl acetate (220 mL) wascooled in an ice-bath. Acetic anhydride (24.52 mL, 0.2421 mol), pyridine (16.16 mL, 0.1998 mol) and4-(dimethylamino)pyridine (100 mg, 0.8186 mmol) were added and the reaction stirred at 0 C for60 min and then at room temperature overnight. Formic acid (5.12 mL, 0.1357 mmol) was added andthe reaction poured onto ice (ca. 500 g). The volume was increased by the addition of further ethylacetate (300 mL) and the organic phase separated and washed with water (2 × 200 mL), sat. aq. NaHCO3(100 mL), further water (2 × 200 mL), and then dried and evaporated to a white solid. Recrystallization ofthe product from 5:1 (v/v) EtOAc/hexane (120 mL) gave 2 crops of 3,5-diacetoxybenzoic acid (combinedweight 17.07 g, 72%) as a white powder. Rf 0.20 (1:1 EtOAc/hexane), 0.39 (3:1 EtOAc/hexane); mp161-162 C (lit. [27] mp: 157-159 C); δH (CDCl3) 2.29 (s, 6H, 2 × OAc), 7.18 (pseudo t, 1H,J = 2.1 Hz, 4-H) and 7.70 (pseudo d, 2H, J = 2.1 Hz, 2-H, 6-H); δC (CD3OD) 18.43, 118.94, 119.02,131.70, 150.19, 165.46 and 168.17; m/z (ESI) 261 ([M + Na]+, 100%).
34%	for 6h;Reflux;	A 500 mL round bottom flask was charged with 3,5-dihydroxybenzoic acid (77.00 g,0.50 mol) and acetic anhydride (200 mL). The reaction mixture was heated to reflux, asthe temperature increased the dihydroxy acid gradually dissolved into solution and themixture was left to reflux for 6 h. A brown solution was obtained containing a small amountof insoluble material; the excess acetic anhydride and acetic acid by-product were removedunder reduced pressure, the compound dissolved in refluxing chloroform (200 mL) andfiltered hot. Petroleum ether (70 mL) was then added to the mother liquor, precipitating awhite solid. The mixture was left overnight, and a white product was isolated by filtration,which was thoroughly washed with petroleum ether. Yield: 40.60 g, 34%; 1H NMR (CDCl3) 10.19 (br s, 1H, -COOH), 7.76 (d, 2H, Ar o-CH), 7.22 (t, 1H, Ar p-CH), 2.31 (s, 6H, -CH3);13C NMR (CDCl3, 300 MHz) 170.0 (COOH), 168.8 (C=O), 151.3 (m-Ar), 131.4 (i-Ar), 122.1(p-Ar), 121.0 (o-Ar), 21.0 (CH3); IR (cm1) 3400-2400, 1765 (COOR), 1687 (COOH), 1603;ES-MS, 237 (M+); MP 160-162 C.

References: [1]Patent: CN105884580,2016,A .Location in patent: Paragraph 0007; 0011; 0012.
[2]European Journal of Medicinal Chemistry,2019,vol. 179,p. 233 - 245.
[3]Tetrahedron Letters,2003,vol. 44,p. 4819 - 4822.
[4]Patent: US2008/280989,2008,A1 .Location in patent: Page/Page column 2; 3.
[5]Patent: WO2007/21067,2007,A1 .Location in patent: Page/Page column 4-5; 8.
[6]Patent: US2012/22284,2012,A1 .Location in patent: Page/Page column 2.
[7]Patent: EP2404891,2012,A1 .Location in patent: Page/Page column 4.
[8]Journal of Medicinal Chemistry,2007,vol. 50,p. 5685 - 5695.
[9]Archiv der Pharmazie,2021,vol. 354.
[10]Tetrahedron Letters,2006,vol. 47,p. 5811 - 5814.
[11]Molecules,2015,vol. 20,p. 17601 - 17613.
[12]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2037 - 2047.
[13]Journal of Organic Chemistry,2013,vol. 78,p. 5364 - 5371.
[14]Molecules,2021,vol. 26.
[15]Journal fur praktische Chemie (Leipzig 1954),1933,vol. <2> 136,p. 205,209.
[16]Chemische Berichte,1926,vol. 59,p. 234.
[17]Journal of Chemical Research, Miniprint,1985,p. 451 - 466.
[18]Journal of the Indian Chemical Society,1998,vol. 75,p. 810 - 822.
[19]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 1402 - 1407.
[20]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1532 - 1533.

3
[ 99-10-5 ]
[ 75-36-5 ]
[ 35354-29-1 ]

References: [1]Journal of the American Chemical Society,1992,vol. 114,p. 3346 - 3355.

4
[ 35354-29-1 ]
[ 35354-30-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; iodine; In tetrahydrofuran; at 0℃;Reflux;	To a 250 mL three-necked flask was added 50 mL of THF,3.15 g (0. 082 mol) of NaBH4, 2.38 g (0.1 mol) of the previous product was added,60 ml of THF solution containing 9 g (0. 036 mol) of I2 was slowly added dropwise at 0 C, followed by the addition of 4.67 g (0.02 mol) of the previous product, followed by heating and refluxing.After completion of the reaction, the mixture was concentrated under reduced pressure, 100 mL of a saturated NaHCO3 solution was added,Extracted with ether, the combined organic layer, dried over anhydrous magnesium sulfate, filtered, concentrated, recrystallized from hot water,A white crystal of 3. 5 g was obtained in a yield of 83.2%.

References: [1]Tetrahedron,1972,vol. 28,p. 1107 - 1111.
[2]Patent: CN105884580,2016,A .Location in patent: Paragraph 0007; 0011; 0013.

5
[ 35354-29-1 ]
(S)-1-((S)-2-Amino-3-methyl-butyryl)-pyrrolidine-2-carboxylic acid (3,3,3-trifluoro-2-hydroxy-1-isopropyl-propyl)-amide [ No CAS ]
Acetic acid 3-acetoxy-5-{(S)-2-methyl-1-[(S)-2-(3,3,3-trifluoro-2-hydroxy-1-isopropyl-propylcarbamoyl)-pyrrolidine-1-carbonyl]-propylcarbamoyl}-phenyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1876 - 1885.

7
[ 50786-93-1 ]
[ 35354-29-1 ]
acetic acid 3-acetoxy-5-(6-amino-3-methyl-2,4-dioxo-1-phenyl-1,2,3,4-tetrahydro-pyrimidin-5-ylcarbamoyl)-phenyl ester [ No CAS ]