75792-33-5|3-Isopropoxybenzaldehyde| Ambeed

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Quality Control of [ 75792-33-5 ] Purity: 98% SDS Specification

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Product Details of [ 75792-33-5 ]

CAS No. :	75792-33-5
Formula :	C₁₀H₁₂O₂
M.W :	164.20
SMILES Code :	O=CC1=CC=CC(OC(C)C)=C1
MDL No. :	MFCD01922005
Boiling Point :	No data available
InChI Key :	NOBKCEXLDDGYID-UHFFFAOYSA-N
Pubchem ID :	712914

Safety of [ 75792-33-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317
Precautionary Statements:	P261-P272-P280-P302+P352-P333+P313-P363-P501

Application In Synthesis of [ 75792-33-5 ]

* 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 [ 75792-33-5 ]

[ 75792-33-5 ] Synthesis Path-Downstream 1~35

1
[ 141-82-2 ]
[ 75792-33-5 ]
[ 58420-22-7 ]

References: [1]Journal of the Chemical Society,1955,p. 461,464.
Journal of the Chemical Society,1959,p. 1027,1030.

2
[ 75792-33-5 ]
[ 114-70-5 ]
3<i>t</i>-(3-isopropoxy-phenyl)-2-phenyl-acrylic acid [ No CAS ]

References: [1]Journal of the Chemical Society,1950,p. 1913,1915.

3
[ 75-30-9 ]
[ 100-83-4 ]
[ 75792-33-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 6h;	3-hydroxybenzaldehyde (61A) (3.05 g, 25.0 mmol)Dissolved in N,N-dimethylformyl (30mL), and then Potassium carbonate (6.9 g, 50.0 mmol) and iodoisopropane(5.09 g, 30.0 mmol) was added to the reaction, and the reaction was carried out at 50 C for 6 hours. The reaction was cooled to 0 C and water (90 mL) was added.The aqueous phase was extracted with methyl tert-butyl ether (30 mL×3) and the organic phases were combined.Wash with saturated sodium chloride (30 mL × 1),Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate to give3-Isopropoxybenzaldehyde (61B) (3.9 g, yield: 95%).
85%	With potassium carbonate; In N,N-dimethyl-formamide; for 42h;	A solution of 3-hydroxybenzaldehyde (67 g, 549 mmol), 2-iodopropane (100 g, 588 mmol) and K2CO3 (130 g, 942 mmol) in 400 mL DMF was stirred for 18 h. To the above solution was added 2-iodopropane (20 g, 117 mmol) and K2CO3 (20 g, 145 mmol) and the mixture was stirred for another 24 h. The reaction mixture was poured into 300 mL water which was extracted with EtOAc (200 mL×3). The combined organic layers were washed with water (100 mL×3), dried over Na2SO4, filtered, and concentrated in vacuo to afford 77 g (85% yield) of 3-isopropoxybenzaldehyde as an oil. 1H NMR (300 MHz, CDCl3) δ 1.29-1.31 (d, 6H) 4.5-4.6 (m, 1H) 7.0-7.1 (m, 1H) 7.3-7.4 (m, 3H).
71%	With potassium carbonate; In ethanol; at 60℃; for 22h;Inert atmosphere;	This method of alkylation is similar to that described in the Journal of Medicinal Chemistry (2002), 45(18), 3891-3904. Dissolved 3-hydroxy benzaldehyde (0.500 g, 4.094 mmole) in 10 mL EtOH at room temperature under argon, and magnetically stirred. Added K2CO3. (1.132 g,8.189 mmole), then 2-iodopropane (0.819 mL, 8.819 mmole). Warmed to 60 C. After 18 hours, added a second equivalent of alkyl iodide (0.819 mL, 8.189 mmole) and continued heating at 60 C. After 4 hours, cooled to room temperature. Concentrated in vacuo. Partitioned residue between EtOAc, and H2O. Washed organic layer with 1 M NaOH, 2x 20 mL, dried organic layer over MgSO4, filtered and concentrated in vacuo. Yield 0.48g, 71%.The material was taken on immediately to the next step.

62%		172 (1.99 g, 16.3 mmol) was added to a solution of K2CO3(4.08 g, 29.5 mmol) in acetone (40 mL) at 0 C under Ar, then thereaction was stirred for 15 min. After 2-iodopropane (3.32 mL,32.8 mmol) was added to the solution, the resulting mixture washeated until reflux began this being maintained for 9 h. The reactionwas quenched with H2O (20 mL) and extracted with EtOAc(3 x 30 mL). The organic layers were washed with H2O (20 mL)and brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo.The residue was purified by silica gel CC (EtOAc/hexane,10:90) to afford 3-isopropoxybenzaldehyde (76) (1.61 g,9.78 mmol, 62%) as a yellow oil: 1H-NMR (CDCl3, 400 MHz) d:1.36 (d, J = 5.6 Hz, 6H, -CH3), 4.63 (heptet, J = 5.6 Hz, 1H, -CH-(CH3)2), 7.15 (m, 1H, Ar-H), 7.38 (brs, 1H, Ar-H), 7.42-7.43 (m,2H, Ar-H), 9.97 (s, 1H, -CHO); spectral data were in agreementwith those in the literature (Garca-Daz et al., 2011).
		N-(2-(3-Isopropoxy)phenethyl)-N'-(2-thiazolyl)thiourea 3-Isopropoxybenzaldehyde was prepared from 3-hydroxybenzaldehyde and isopropyl iodide analogous to the procedure described in Example 361.
	With potassium carbonate; In ethanol; at 60℃; for 22h;	This method of alkylation is similar to that described in J Med Chem (2002), 45(18), 3891-3904. Dissolved 3-Hydroxy benzaldehyde (0.500g, 4.094 mmole) in 10 mL EtOH at rt, under Argon, and magnetically stirred. Added K2CO3. (1.132g, 8.189mmole), then 2-iodopropane (0.819 mL, 8.819 mmole). Warmed to 6O0C. After 18 hr, added a second equivalent of alkyl iodide of (0.819 mL, 8.189 mmole) and continued heating at 6O0C. After 4 hr, cooled to rt and concentrated in vacuo. Partitioned residue between EtOAc, and H2O. Washed organic layer with 1 M NaOH, 2x 2OmL , dried organic layer over MgSO4, filtered and concentrated in vacuo to give the aldehyde.
	With potassium carbonate; In isopropyl alcohol; for 8h;Heating / reflux;	Step 10a: 3-isopropoxybenzaldehyde; To a 1 molar solution of 3-hydroxybenzaldehyde (10Og, 0.819 moles) in isopropyl alcohol (820 mL) was added 2-iodopropane (146.2g, 0.860 moles) followed by powdered potassium carbonate (339.5g, 0.457 moles) and the mixture was heated to reflux under nitrogen for a minimum of 8 hrs. The reaction was complete by TLC. Water was added to the cooled reaction until all salts were dissolved. The mixture was extracted with ether three times. The combined ether extracts were washed with water, 2 M NaOH and again with water until clear (three times) then brine. The organic layer was dried over magnesium sulfate and filtered and evaporated to give the desired product as a pale oil. lH NMR (400 MHz, CDC13) δ 9.95 (s, IH), 7.2 (m, 3H), 7.12 (m, IH), 4.6 (m, IH), 1.32 (bs, 6H) ppm. LCMS ion fragment = 164.1
	With potassium carbonate; In isopropyl alcohol; for 8h;Heating / reflux;	3-lsopropoxy-benzaldehvde.A solution of 3-hydroxybenzaldehyde (4.5 g) and 2-iodopropane (3.72 ml_) in 2-propanol (40 mL) was treated with K2CO3 (16.09 g). After 8 h at reflux, water (40 mL) was added and the mixture was extracted with Et2θ (3x 25mL). The combined organic layers were washed with water (25 mL), 2 M NaOH (25 mL), water (4x25 mL), and satd. aq. NaCI (25 mL). The organic phase was dried (Na2SO4), and concentrated to give the title compound as a pale orange oil (3.31 g). 1H NMR (CDCI3): 9.96 (s, 1H), 7.45-7.41 (m, 2H), 7.38-7.37 (m, 1H), 7.17-7.13 (m, 1 H), 4.68-4.59 (septet, 1 H1 J= 6.1 Hz), 1.37-1.35 (d, 6H, J= 6.1 Hz).
	With sodium carbonate; In N,N-dimethyl-formamide; at 50℃; for 100h;	A 75 mL mini-block tube equipped with a magnetic stirrer bar was charged with 6.16 g (50.4 mmol) of 3-hydroxybenzaldehyde, 4.40 mL (8.58 g, 55.0 mmol) of isopropyl iodide 30 mL of dimethylformamide and 6.05 g (57.1 mmol) of sodium carbonate. The slurry was heated to 500C.After 40 hours the reaction was only 50% complete so another 3 ml (5.85 g, 37.4 mmol) isopropyl iodide was added. After 60 more hours another 3 mL (5.85 g, 37.4 mmol) isopropyl iodide and 3 g (28.5 mmol) of sodium carbonate were added. The reaction mixture was cooled to 25C and diluted with methyl t-butyl ether (MTBE) and water. The organic layer was decanted off. The aqueous phase was rinsed with MTBE, again decanting off the organic layer. The combined organic layers were washed with 2N aqueous sodium hydroxide (3 X 30 mL) and brine (1 X 30 mL), dried over sodium sulfate and concentrated to give 3-Isopropoxybenzaldehyde which was used as (following the above procedure for 3-(4-t-butylphenyl)propanoic acid (Example 6) to prepare 3-(3- Isopropoxyphenyl)propanoic acid (1.31 g) as an off-white solid. IH NMR (d6-DMSO): δ 12.0, bs, IH (COOH); δ 7.03, t, IH, (arylH meta to O-i-Pr); δ 6.6, m, 3H (other arylH's); δ 4.45, hept, IH, (OCH); 2.65, t, 2H, (CH2 α to aryl); δ 2.38, t, 2H (CH2 α to COOH); δ 1.12, d, 6H (CH3's). 13C NMR (d6-DMSO): 173.70, 157.40, 142.46, 129.26, 120.17, 115.54, 112.93, 68.77, 35.09, 30.31, 21.84.

References: [1]Patent: CN109206417,2019,A .Location in patent: Paragraph 2183; 2186-2191.
[2]Patent: US2008/194535,2008,A1 .Location in patent: Page/Page column 36-37.
[3]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 4812 - 4819.
[4]Journal of Medicinal Chemistry,2002,vol. 45,p. 3891 - 3904.
[5]Phytochemistry,2013,vol. 96,p. 132 - 147.
[6]Journal of the Chemical Society,1955,p. 461,464.
Journal of the Chemical Society,1959,p. 1027,1030.
[7]Patent: US5593993,1997,A .
[8]Patent: WO2006/44497,2006,A2 .Location in patent: Page/Page column 55.
[9]Patent: WO2007/11810,2007,A1 .Location in patent: Page/Page column 37; 42.
[10]Patent: WO2007/140005,2007,A2 .Location in patent: Page/Page column 28.
[11]Patent: WO2008/112368,2008,A2 .Location in patent: Page/Page column 35.

4
[ 100-83-4 ]
[ 75-26-3 ]
[ 75792-33-5 ]

Yield	Reaction Conditions	Operation in experiment
44.2 g (82%)	With potassium carbonate; In water; N,N-dimethyl-formamide;	(a) A mixture of isopropyl bromide (36.8 mL, 0.39 mol), m-hydroxybenzaldehyde (40 g, 0.327 mol), and potassium carbonate (53.9 g, 0.39 mol) in 200 mL of DMF was stirred at room temperature for 12 h. After adding additional isopropyl bromide (20 mL) and potassium carbonate (10 g), the reaction mixture was stirred at room temperature for 18 h and then heated at 50 C. for 1 h. Water (500 mL) was added to the mixture, the red oil formed was removed by decantation, and the aqueous layer was extracted with methylene chloride (3*250 mL) and the combined organic layers were washed with 200 mL of 2N NaOH solution, brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was distilled (0.75 mm/80-100 C.) to afford 44.2 g (82%) of m-isopropoxybenzaldehyde as a colorless oil.
	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃;	To a 500mL three necked flask was added 200mL DMF, to the stirred mixture was added 3-hydroxybenzaldehyde (5g,40.9mmol, 1.Oeq), K2C03 (15.3g, 11O.5mol, 2.7eq) and 2-bromopropane (6.5g,53.2mmol, 1.3eq). The reaction was heated to 70C overnight. TLC (PE: EA=10:1, Rf=0.5) showed the reaction was completed. The reaction was allowed to cool to room temperature. The reaction mixture was poured onto 500mL crush ice, the mixture was stirred for 10mm, extracted with EA (l5OmL3). The combined organiclayers were washed with 10% LiC1 aqueous solution (l5OmL2) and dried over Na2SO4, filtered and concentrated in vacuum. The filtrate was concentrated in vacuum and purified by column chromatography on silica gel eluted with PE:EA= 50:1 to yield the title product (6g, HPLC: 94.8%) as a light yellow oil. (Yield: 89.5%).

References: [1]European Journal of Organic Chemistry,2011,p. 3165 - 3170.
[2]Molecules,2015,vol. 20,p. 12512 - 12524.
[3]Heterocycles,1994,vol. 39,p. 503 - 508.
[4]Liebigs Annalen,1996,p. 2045 - 2058.
[5]European Journal of Organic Chemistry,2015,vol. 2015,p. 6324 - 6332.
[6]Journal of the Chemical Society,1950,p. 1913,1915.
[7]Patent: US5554620,1996,A .
[8]Patent: WO2018/208630,2018,A1 .Location in patent: Page/Page column 53.

5
[ 75792-33-5 ]
[ 162147-12-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bromine; anhydrous Sodium acetate; In dichloromethane; for 1.5h;	To a stirred mixture of 3-(propan-2-yloxy)benzaldehyde (9.73 g,0.0593 mol) and AcONa (15 g) in CH2Cl2 (200 mL) cooled inan ice bath, was added dropwise a solution of Br2 (3.19 mL,0.0623 mol) in CH2Cl2 (20 mL).After 1 h at 0 C, another amount ofBr2 (3.19 mL, 0.0623 mol) dissolved in CH2Cl2 (20 mL) was addeddropwise.After 30 min, the wholewaswashed successively withwater and a 1:1 mixture of 5% NaHCO3 and 10% Na2S2O3 solutions,dried over Na2SO4, and concentrated. The oily residue waschromatographed on silica gel eluted with hexane/i-Pr2O (10:1)to give 12 (12.26 g, 0.05043 mol, 85%) as a pale oil. 1H NMR (400MHz) 1.34 (6H, d, J = 5.8 Hz, CH(CH3)2), 4.59 (1H, sept, J = 5.8 Hz,OCH(CH3)2), 6.99 (1H, dd, J = 8.8, 2.9 Hz, H-4), 7.40 (1H, d, J = 2.9 Hz,H-6), 7.50 (1H, d, J = 8.8 Hz, H-3), 10.29 (1H, s, CHO). 13C NMR (100MHz) 21.7 (CH3), 70.4 (CH), 114.5 (CH), 117.4 (C), 124.4 (CH), 133.8(C), 134.5 (CH), 157.5 (C), 191.7 (CH). IR (KBr) max 1110, 1230, 1272,1387, 1469, 1692, 2976 cm-1. HRMS (DART+): calcd for C10H12BrO2[M + H]+, 243.0021; found, 242.9995.
85%	With bromine; anhydrous Sodium acetate; In dichloromethane; for 1.5h;	To a stirred mixture of 3-(propan-2-yloxy)benzaldehyde (9.73 g,0.0593 mol) and AcONa (15 g) in CH2Cl2 (200 mL) cooled inan ice bath, was added dropwise a solution of Br2 (3.19 mL,0.0623 mol) in CH2Cl2 (20 mL).After 1 h at 0 C, another amount ofBr2 (3.19 mL, 0.0623 mol) dissolved in CH2Cl2 (20 mL) was addeddropwise.After 30 min, the wholewaswashed successively withwater and a 1:1 mixture of 5% NaHCO3 and 10% Na2S2O3 solutions,dried over Na2SO4, and concentrated. The oily residue waschromatographed on silica gel eluted with hexane/i-Pr2O (10:1)to give 12 (12.26 g, 0.05043 mol, 85%) as a pale oil. 1H NMR (400MHz) 1.34 (6H, d, J = 5.8 Hz, CH(CH3)2), 4.59 (1H, sept, J = 5.8 Hz,OCH(CH3)2), 6.99 (1H, dd, J = 8.8, 2.9 Hz, H-4), 7.40 (1H, d, J = 2.9 Hz,H-6), 7.50 (1H, d, J = 8.8 Hz, H-3), 10.29 (1H, s, CHO). 13C NMR (100MHz) 21.7 (CH3), 70.4 (CH), 114.5 (CH), 117.4 (C), 124.4 (CH), 133.8(C), 134.5 (CH), 157.5 (C), 191.7 (CH). IR (KBr) max 1110, 1230, 1272,1387, 1469, 1692, 2976 cm-1. HRMS (DART+): calcd for C10H12BrO2[M + H]+, 243.0021; found, 242.9995.

References: [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 6324 - 6332.
[2]European Journal of Organic Chemistry,2011,p. 3165 - 3170.
[3]Bioscience, Biotechnology and Biochemistry,2021,vol. 85,p. 181 - 191.
[4]Bioscience, Biotechnology and Biochemistry,2021,vol. 85,p. 181 - 191.
[5]Heterocycles,1994,vol. 39,p. 503 - 508.

6
[ 75792-33-5 ]
[ 75-07-0 ]
(S)-2-hydroxy-1-(3-isopropoxyphenyl)propan-1-one [ No CAS ]

References: [1]Chemistry - A European Journal,2000,vol. 6,p. 1483 - 1495.
[2]European Journal of Organic Chemistry,2000,p. 2161 - 2170.

7
[ 75792-33-5 ]
[ 3586-12-7 ]
(3-isopropoxy-benzyl)-(3-phenoxy-phenyl)-amine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3891 - 3904.

8
[ 75792-33-5 ]
[ 371222-24-1 ]
[ 823236-47-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 93 - 98.

9
[ 696-59-3 ]
[ 75792-33-5 ]
2,3-bis-(3-isopropyloxybenzylidene)succinaldehyde [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 2498 - 2506.

10
[ 75792-33-5 ]
3[(3-phenoxyphenyl)[[3-(isopropoxy)phenyl]methyl]amino]-1,1,1-trifluoro-2-propanol [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3891 - 3904.

11
[ 75792-33-5 ]
[ 162147-14-0 ]