(2-propan-2-yloxyphenyl)methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-hydroxybenzaldehyde (0.5 ml) in dimethylformamide (5 ml), 1.35 ml of 2-bromopropane and 1.98 g of potassium carbonate were added, and the reaction solution was stirred overnight at room temperature. To the reaction solution was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in methanol (5 ml), 362 mg of sodium borohydride was added under ice-cooling, and the reaction solution was stirred at room temperature for 30 minutes. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford the title compound as a colorless oil. the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil cooling the reaction solution was stirred at room temperature for 30 minutes the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50))

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-hydroxybenzyl alcohol (21.04 g, 1 equiv., available from Aldrich Chemical Company), 2-isopropyl iodide (32.3 mL, 1.9 equiv., available from Aldrich Chemical Company) and K2CO3 (71.42 g, 3 equiv.) in ethanol was refluxed for 3 hours. On cooling the reaction mixture was filtered and the solvent removed under reduced pressure and replaced with dichloromethane, and then filtered and the solvent removed to give the title compound as an oil (27.751 g, 99%). 1H NMR (300 MHz, CDCl3): δ 1.37 (d, 6H, J=6.0 Hz), 3.55 (bs, 1H), 4.50-4.70 (m, 3H), 6.78-6.90 (m, 2H), 7.15-7.25 (m, 2H). was refluxed for 3 hours On cooling the reaction mixture was filtered the solvent removed under reduced pressure filtered the solvent removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-hydroxybenzaldehyde (0.5 ml) in dimethylformamide (5 ml), 1.35 ml of 2-bromopropane and 1.98 g of potassium carbonate were added, and the reaction solution was stirred overnight at room temperature. To the reaction solution was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in methanol (5 ml), 362 mg of sodium borohydride was added under ice-cooling, and the reaction solution was stirred at room temperature for 30 minutes. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford the title compound as a colorless oil. the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil cooling the reaction solution was stirred at room temperature for 30 minutes the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50))

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-hydroxybenzaldehyde (0.5 ml) in dimethylformamide (5 ml), 1.35 ml of 2-bromopropane and 1.98 g of potassium carbonate were added, and the reaction solution was stirred overnight at room temperature. To the reaction solution was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in methanol (5 ml), 362 mg of sodium borohydride was added under ice-cooling, and the reaction solution was stirred at room temperature for 30 minutes. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford the title compound as a colorless oil. the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil cooling the reaction solution was stirred at room temperature for 30 minutes the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50))

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-hydroxybenzyl alcohol (21.04 g, 1 equiv., available from Aldrich Chemical Company), 2-isopropyl iodide (32.3 mL, 1.9 equiv., available from Aldrich Chemical Company) and K2CO3 (71.42 g, 3 equiv.) in ethanol was refluxed for 3 hours. On cooling the reaction mixture was filtered and the solvent removed under reduced pressure and replaced with dichloromethane, and then filtered and the solvent removed to give the title compound as an oil (27.751 g, 99%). 1H NMR (300 MHz, CDCl3): δ 1.37 (d, 6H, J=6.0 Hz), 3.55 (bs, 1H), 4.50-4.70 (m, 3H), 6.78-6.90 (m, 2H), 7.15-7.25 (m, 2H). was refluxed for 3 hours On cooling the reaction mixture was filtered the solvent removed under reduced pressure filtered the solvent removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-hydroxybenzaldehyde (0.5 ml) in dimethylformamide (5 ml), 1.35 ml of 2-bromopropane and 1.98 g of potassium carbonate were added, and the reaction solution was stirred overnight at room temperature. To the reaction solution was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil. To a solution of the crude product in methanol (5 ml), 362 mg of sodium borohydride was added under ice-cooling, and the reaction solution was stirred at room temperature for 30 minutes. To the reaction solution was added 10% aqueous citric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50)) to afford the title compound as a colorless oil. the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure to afford a crude product as a yellow oil cooling the reaction solution was stirred at room temperature for 30 minutes the mixture was extracted with ethyl acetate The combined organic layers were washed with a saturated saline solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the residue obtained was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (98:2-50:50))