* 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.
Stage #1: at 8 - 20℃; for 1 h; Stage #2: With ammonium chloride In tetrahydrofuran; water; toluene
1-(4-methoxy-phenyl)-2-methyl-propan-1-ol A solution of 1.5 ml 4-methoxy-benzaldehyde in 10 ml of toluene is added dropwise at 8° C. to 7.4 ml of a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran. Then the mixture is allowed to come up to ambient temperature and stirred for 1 hour. Then the reaction is stopped by the addition of semisaturated aqueous ammonium chloride solution. The phases are separated and the aqueous phase is extracted with toluene. The combined organic phases are washed with semisaturated aqueous ammonium chloride solution and dried on magnesium sulphate. The solvents are eliminated in vacuo and the product thus obtained is further reacted directly. Yield: 2.12 g (95percent of theory) HPLC (method 1): retention time=3.22 min.
Reference：
[1] Patent: US2011/269737, 2011, A1, . Location in patent: Page/Page column 63
[2] Australian Journal of Chemistry, 1986, vol. 39, # 12, p. 2095 - 2110
[3] Patent: US2597446, 1949, ,
2
[ 2040-20-2 ]
[ 18228-46-1 ]
Yield
Reaction Conditions
Operation in experiment
76%
With sodium borohydrid In ethanol; dichloromethane; water
EXAMPLE 5 Preparation of 1-(4'-Methoxyphenyl)-2-methyl-1-propanol A solution of 4-methoxyisobutyrophenone (14.6 grams, 0.082 moles) in ethanol (150 ml) was prepared. Sodium borohydride (2.6 grams, 0.069 moles) was added to the solution in portions over a one hour period under nitrogen. The reaction mass was stirred at room temperature for about two hours. Ethanol was removed under reduced pressure. The reaction mass was added to water (200 ml) and acidified with 10percent hydrochloric acid (50 ml). The mixture was then extracted with methylene chloride (3 times with 100 ml of methylene chloride each time). The combined organic extract was collected, dried with anhydrous magnesium sulfate and concentrated to yield 1-(4'-methoxyphenyl)-2-methyl-1-propanol having a purity of 90percent (12.5 grams corresponding to 76percent yield). The crude product was purified by vacuum distillation (boiling point 89°-91° C. at 0.5 mmHg).
76%
With sodium borohydrid In ethanol; water
Sodium borohydride (2.6 g, 0.069 mol) was added in portions over a 1 h period to a solution of 4-methoxyisobutyrophenone (14.6 g, 0.082 mol) in ethanol (150 mL) under nitrogen. The reaction was stirred at room temperature for 2 h. Ethanol was removed under reduced pressure. The reaction was added to water (200 mL) and acidified with 10percent HCl (50 mL). The mixture was extracted with methylene chloride (3*100 mL) and the combined organic extract was collected, dried (anhy. MgSO4), and concentrated to afford 1-(4'-methoxyphenyl)-2-methyl-1-propanol in 90percent purity (12.5 g, 76percent yield). The crude product was purified by vacuum distillation: bp 89°-91° C. at 0.5 mm Hg.
Reference：
[1] Australian Journal of Chemistry, 1986, vol. 39, # 12, p. 2095 - 2110
[2] Patent: US5179229, 1993, A,
[3] Patent: US5012007, 1991, A,
[4] Tetrahedron, 1968, vol. 24, p. 421 - 425
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1992, vol. 31, # 3, p. 156 - 162
3
[ 123-11-5 ]
[ 75-26-3 ]
[ 18228-46-1 ]
Reference：
[1] Journal of the American Chemical Society, 1980, vol. 102, # 27, p. 7926 - 7927
[2] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1973, p. 301 - 310
[3] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1668 - 1674
[4] Organic Letters, 2014, vol. 16, # 17, p. 4650 - 4653
[5] Organic Letters, 2018, vol. 20, # 10, p. 2906 - 2910
4
[ 75-29-6 ]
[ 123-11-5 ]
[ 18228-46-1 ]
Reference：
[1] Journal of Organic Chemistry, 2006, vol. 71, # 10, p. 3967 - 3969
1-(4-methoxy-phenyl)-2-methyl-propan-1-ol A solution of 1.5 ml 4-methoxy-benzaldehyde in 10 ml of toluene is added dropwise at 8 C. to 7.4 ml of a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran. Then the mixture is allowed to come up to ambient temperature and stirred for 1 hour. Then the reaction is stopped by the addition of semisaturated aqueous ammonium chloride solution. The phases are separated and the aqueous phase is extracted with toluene. The combined organic phases are washed with semisaturated aqueous ammonium chloride solution and dried on magnesium sulphate. The solvents are eliminated in vacuo and the product thus obtained is further reacted directly. Yield: 2.12 g (95% of theory) HPLC (method 1): retention time=3.22 min.
With sodium borohydrid; In ethanol; dichloromethane; water;
EXAMPLE 5 Preparation of 1-(4'-Methoxyphenyl)-2-methyl-1-propanol A solution of 4-methoxyisobutyrophenone (14.6 grams, 0.082 moles) in ethanol (150 ml) was prepared. Sodium borohydride (2.6 grams, 0.069 moles) was added to the solution in portions over a one hour period under nitrogen. The reaction mass was stirred at room temperature for about two hours. Ethanol was removed under reduced pressure. The reaction mass was added to water (200 ml) and acidified with 10% hydrochloric acid (50 ml). The mixture was then extracted with methylene chloride (3 times with 100 ml of methylene chloride each time). The combined organic extract was collected, dried with anhydrous magnesium sulfate and concentrated to yield 1-(4'-methoxyphenyl)-2-methyl-1-propanol having a purity of 90% (12.5 grams corresponding to 76% yield). The crude product was purified by vacuum distillation (boiling point 89-91 C. at 0.5 mmHg).
76%
With sodium borohydrid; In ethanol; water;
Sodium borohydride (2.6 g, 0.069 mol) was added in portions over a 1 h period to a solution of 4-methoxyisobutyrophenone (14.6 g, 0.082 mol) in ethanol (150 mL) under nitrogen. The reaction was stirred at room temperature for 2 h. Ethanol was removed under reduced pressure. The reaction was added to water (200 mL) and acidified with 10% HCl (50 mL). The mixture was extracted with methylene chloride (3*100 mL) and the combined organic extract was collected, dried (anhy. MgSO4), and concentrated to afford 1-(4'-methoxyphenyl)-2-methyl-1-propanol in 90% purity (12.5 g, 76% yield). The crude product was purified by vacuum distillation: bp 89-91 C. at 0.5 mm Hg.
With triethylsilane; trifluoroacetic acid; at 0 - 10℃; for 1h;
1-isobutyl-4-methoxy-benzene 1.9 g <strong>[18228-46-1]1-(4-methoxy-phenyl)-2-methyl-propan-1-ol</strong> are dissolved in 30 ml dissolved, cooled to 0 C. and mixed with 3.37 ml triethylsilane. The mixture is stirred for 10 minutes and then 1.62 ml trifluoroacetic acid are added. Within 1 hour the mixture is heated to 10 C., then the reaction is stopped by the addition of water and the phases are separated. The organic phase is washed with saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and then dried on magnesium sulphate. The solvents are eliminated in vacuo and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 95:5 to 80:20). Yield: 1.48 g (85% of theory) HPLC (method 1): retention time=4.81 min.
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