2-(3-羟基-3-甲基丁基)苯酚

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 16 g (89 mmol) of 4-(2-hydroxyphenyl)-2-methyl-2-butanol, (Compound 55), 40 ml of conc. H2SO4 and 160 ml of water was heated at reflux for 4 hours. The mixture was cooled, diluted with 300 ml of water and extracted with 2×100 ml of hexane. The organic extracts were combined, washed successively with water and saturated NaCl solution and then dried. The solution was then filtered and the filtrate concentrated in-vacuo to give the title compound as a yellow oil. PMR (CDCl3) : & 1.32 (6H, s), 1.78 (2H, t, J~6.8 Hz), 2.76 (2H, t, J~6.8 Hz), 6.74-6.85 (2H, m), 7.01-7.12 (2H, m). was heated at reflux for 4 hours The mixture was cooled extracted with 2×100 ml of hexane washed successively with water and saturated NaCl solution dried The solution was then filtered the filtrate concentrated in-vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To an ice-cooled solution of methyl magnesium bromide in ether (104 ml × 2.7M; 0.28 mole) was added slowly, under nitrogen, a solution of 13.8 g (0.093 mole) of dihydrocoumarin (Compound 28, Scheme 8) in 230 ml of dry ether. The cooling bath was then removed and the mixture stirred for a further 16 hours. The reaction mixture was then poured onto 300 g of ice and 10 ml of conc. H2SO4 and the mixture was stirred to ensure dissolution. The organic layer was then separated and the aqueous layer was extracted with 2×100 ml of ether. The organic layers were combined and washed successively with 70 ml portions of water, saturated NaHCO3, 2M Na2S2O3 and saturated NaCl and then dried (Na2SO4). The solution was then filtered and the filtrate concentrated in-vacuo to give the title compound as a white solid. PMR (CDCl3) : & 1.30 (6H, s), 1.80 (2H, t, J~7.5 Hz), 2.12 (1H, broad s), 2.73 (2H, t, J~7.5 Hz), 6.80-6.87 (2H, m), 7.00 (1H, broad s), 7.07-7.14 (2H, m). was added slowly, under nitrogen The cooling bath was then removed The reaction mixture was then poured onto 300 g of ice and 10 ml of conc. H2SO4 the mixture was stirred dissolution The organic layer was then separated the aqueous layer was extracted with 2×100 ml of ether washed successively with 70 ml portions of water, saturated NaHCO3, 2M Na2S2O3 and saturated NaCl dried (Na2SO4) The solution was then filtered the filtrate concentrated in-vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To an ice-cooled solution of methyl magnesium bromide in ether (104 ml × 2.7M; 0.28 mole) was added slowly, under nitrogen, a solution of 13.8 g (0.093 mole) of dihydrocoumarin (Compound 28, Scheme 8) in 230 ml of dry ether. The cooling bath was then removed and the mixture stirred for a further 16 hours. The reaction mixture was then poured onto 300 g of ice and 10 ml of conc. H2SO4 and the mixture was stirred to ensure dissolution. The organic layer was then separated and the aqueous layer was extracted with 2×100 ml of ether. The organic layers were combined and washed successively with 70 ml portions of water, saturated NaHCO3, 2M Na2S2O3 and saturated NaCl and then dried (Na2SO4). The solution was then filtered and the filtrate concentrated in-vacuo to give the title compound as a white solid. PMR (CDCl3) : & 1.30 (6H, s), 1.80 (2H, t, J~7.5 Hz), 2.12 (1H, broad s), 2.73 (2H, t, J~7.5 Hz), 6.80-6.87 (2H, m), 7.00 (1H, broad s), 7.07-7.14 (2H, m). was added slowly, under nitrogen The cooling bath was then removed The reaction mixture was then poured onto 300 g of ice and 10 ml of conc. H2SO4 the mixture was stirred dissolution The organic layer was then separated the aqueous layer was extracted with 2×100 ml of ether washed successively with 70 ml portions of water, saturated NaHCO3, 2M Na2S2O3 and saturated NaCl dried (Na2SO4) The solution was then filtered the filtrate concentrated in-vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 16 g (89 mmol) of 4-(2-hydroxyphenyl)-2-methyl-2-butanol, (Compound 55), 40 ml of conc. H2SO4 and 160 ml of water was heated at reflux for 4 hours. The mixture was cooled, diluted with 300 ml of water and extracted with 2×100 ml of hexane. The organic extracts were combined, washed successively with water and saturated NaCl solution and then dried. The solution was then filtered and the filtrate concentrated in-vacuo to give the title compound as a yellow oil. PMR (CDCl3) : & 1.32 (6H, s), 1.78 (2H, t, J~6.8 Hz), 2.76 (2H, t, J~6.8 Hz), 6.74-6.85 (2H, m), 7.01-7.12 (2H, m). was heated at reflux for 4 hours The mixture was cooled extracted with 2×100 ml of hexane washed successively with water and saturated NaCl solution dried The solution was then filtered the filtrate concentrated in-vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To an ice-cooled solution of methyl magnesium bromide in ether (104 ml × 2.7M; 0.28 mole) was added slowly, under nitrogen, a solution of 13.8 g (0.093 mole) of dihydrocoumarin (Compound 28, Scheme 8) in 230 ml of dry ether. The cooling bath was then removed and the mixture stirred for a further 16 hours. The reaction mixture was then poured onto 300 g of ice and 10 ml of conc. H2SO4 and the mixture was stirred to ensure dissolution. The organic layer was then separated and the aqueous layer was extracted with 2×100 ml of ether. The organic layers were combined and washed successively with 70 ml portions of water, saturated NaHCO3, 2M Na2S2O3 and saturated NaCl and then dried (Na2SO4). The solution was then filtered and the filtrate concentrated in-vacuo to give the title compound as a white solid. PMR (CDCl3) : & 1.30 (6H, s), 1.80 (2H, t, J~7.5 Hz), 2.12 (1H, broad s), 2.73 (2H, t, J~7.5 Hz), 6.80-6.87 (2H, m), 7.00 (1H, broad s), 7.07-7.14 (2H, m). was added slowly, under nitrogen The cooling bath was then removed The reaction mixture was then poured onto 300 g of ice and 10 ml of conc. H2SO4 the mixture was stirred dissolution The organic layer was then separated the aqueous layer was extracted with 2×100 ml of ether washed successively with 70 ml portions of water, saturated NaHCO3, 2M Na2S2O3 and saturated NaCl dried (Na2SO4) The solution was then filtered the filtrate concentrated in-vacuo