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Stage #1: With sodium tetrahydroborate In tetrahydrofuran at 20℃; Stage #2: With methanesulfonic acid In tetrahydrofuran at 20 - 70℃;
A solution of 0.5 kg 3-(2-methoxy-5-methylphenyl) -3-phenyl propionic acid in 2.0 L tetrahydrofuran was added drop wise in the suspension of 0.105 kg sodium borohydride in 0.5 L tetrahydrofuran within 2 hrs. After completion of addition, reaction mixture was stirred at RT for 2 hrs. 0.177 kg methanesulfonic acid was added drop wise within 1 hrs. After completion of addition, reaction mixture was stirred at RT for 1 hr. The reaction mixture was stirred at 65-7O0C for 8-10 hrs. After completion of reaction, reaction mixture was cooled at 0-50C. The reaction mixture was acidified with 0.25 L IM aq. HCl up to pH 2-3, and then reaction mixture was extracted with ethyl acetate (1 L x 2). The organic layers were washed with 2.0 L water 2.0 L brine. The solvent was distilled out to dryness at reduced pressure (30-40 mm Hg) to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propanol (Yield: 0.462 kg, 97percent)[167] HPLC Purity > 95percent.
85%
Stage #1: With sodium tetrahydroborate In tetrahydrofuran at 20℃; Stage #2: With sulfuric acid In tetrahydrofuran at 20 - 70℃;
Example 2 [158] Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenyl propanol; [159](III) (IV) [161] [162] A solution of 0.5 kg of 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid in 1.5 L tetrahydrofuran was added drop wise in the suspension of 0.105 Kg of sodium borohydride in 1 L ml tetrahydrofuran under stirring within 2-4 hrs. After completion of addition, reaction mixture was stirred at RT for 2 hrs. 0.181 Kg of Cone. Sulfuric acid was added drop wise within 2-3 hrs. After completion of addition, reaction mixture was stirred at RT for 1-2 hr. The reaction mixture was stirred at 65-7O0C for 6-10 hrs. After completion of reaction, reaction mixture was cooled to 25-3O0C. Saturated brine solution was added to reaction mass and the solution was stirred for 15 min. The organic layer was separated out and distilled it completely. The reaction mass was mixed with aqueous layer and then extracted with dichloromethane (IL x 2). The organic layers were combined and washed with 1 L water ; 1 L brine. The solvent was distilled out to dryness at reduced pressure (30-40 mm Hg) to obtain 3 - (2-methoxy- 5 -methylphenyl) -3 -phenyl propanol.[163] (Yield 0402 Kg, 85percent) [164] HPLC Purity >; 96percent
A reaction mixture of 0.75 kg 3,4-dihydro-6-methyl -4-phenyl-2H-benzopyran-2-one, 0.262 kg sodium hydroxide and 0.93 L DM water was stirred at 60-650C for 2 hrs. The reaction was cooled to RT. 0.825 kg dimethylsulphate was added drop wise to reaction mixture within 1 hr. After the completion of addition, reaction mixture was stirred at same temperature for 2 hrs. Again solution of 0.186 kg sodium hydroxide in 0.93 L DM water was added at RT within 1 hr. The reaction mixture was stirred at 800C for 4 hrs. After completion of reaction, reaction was cooled to RT. 0.3 L Cone, hydrochloric acid was added drop wise to the reaction mixture till washing is neutral. The reaction mixture was stirred for 2 hrs, then filtered & washed with 2.0 L DM water to obtain wet cake. The wet cake was dried at 60-650C for 10-12 hrs to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid (Yield: 0.71 kg, 83%).[159] HPLC Purity: > 95 %.
83%
Example 1[149] Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid; [150](H) (HI)[152] [153] A reaction mixture of 0.75 kg <strong>[40546-94-9]3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-one</strong>, 0.262 kg sodium hydroxide and 0.93 L DM water was stirred at 55-65C for 2-3 hrs. The reaction was cooled to RT. 0.825 kg dimethylsulphate was added drop wise to reaction mixture within 1-2 hr. After the completion of addition, reaction mixture was stirred at same temperature for 1-2 hrs. Again solution of 0.186 kg sodium hydroxide in 0.93 L DM water was added at RT within 1 hr. The reaction mixture was stirred at 70-800C for 3-5 hrs. After completion of reaction, reaction was cooled to RT. 0.3 L Cone, hydrochloric acid was added drop wise to the reaction mixture till washing is neutral. The reaction mixture was stirred for 1-2 hrs, then filtered &; washed with 2.0 L DM water to obtain wet cake. The wet cake was dried at 55-600C for 10-12 hrs to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid.[154] (Yield: 0.71 kg, 83%). [155] HPLC Purity: >; 95 %.
A solution of 0.5 kg 3-(2-methoxy-5-methylphenyl) -3-phenyl propionic acid in 2.0 L tetrahydrofuran was added drop wise in the suspension of 0.105 kg sodium borohydride in 0.5 L tetrahydrofuran within 2 hrs. After completion of addition, reaction mixture was stirred at RT for 2 hrs. 0.177 kg methanesulfonic acid was added drop wise within 1 hrs. After completion of addition, reaction mixture was stirred at RT for 1 hr. The reaction mixture was stirred at 65-7O0C for 8-10 hrs. After completion of reaction, reaction mixture was cooled at 0-50C. The reaction mixture was acidified with 0.25 L IM aq. HCl up to pH 2-3, and then reaction mixture was extracted with ethyl acetate (1 L x 2). The organic layers were washed with 2.0 L water & 2.0 L brine. The solvent was distilled out to dryness at reduced pressure (30-40 mm Hg) to obtain 3-(2-methoxy-5-methylphenyl)-3-phenyl propanol (Yield: 0.462 kg, 97%)[167] HPLC Purity > 95%.
85%
Example 2 [158] Preparation of 3-(2-methoxy-5-methylphenyl)-3-phenyl propanol; [159](III) (IV) [161] [162] A solution of 0.5 kg of 3-(2-methoxy-5-methylphenyl)-3-phenyl propionic acid in 1.5 L tetrahydrofuran was added drop wise in the suspension of 0.105 Kg of sodium borohydride in 1 L ml tetrahydrofuran under stirring within 2-4 hrs. After completion of addition, reaction mixture was stirred at RT for 2 hrs. 0.181 Kg of Cone. Sulfuric acid was added drop wise within 2-3 hrs. After completion of addition, reaction mixture was stirred at RT for 1-2 hr. The reaction mixture was stirred at 65-7O0C for 6-10 hrs. After completion of reaction, reaction mixture was cooled to 25-3O0C. Saturated brine solution was added to reaction mass and the solution was stirred for 15 min. The organic layer was separated out and distilled it completely. The reaction mass was mixed with aqueous layer and then extracted with dichloromethane (IL x 2). The organic layers were combined and washed with 1 L water &; 1 L brine. The solvent was distilled out to dryness at reduced pressure (30-40 mm Hg) to obtain 3 - (2-methoxy- 5 -methylphenyl) -3 -phenyl propanol.[163] (Yield 0402 Kg, 85%) [164] HPLC Purity >; 96%