3-(4-propoxyphenyl)propan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 3-(4-propoxyphenyl)-1-propanol (735 mg) and THF (20 ml) were added at 0° C. triethylamine (1.58 ml) and methanesulfonyl chloride (0.44 ml). The resulting mixture was stirred at 0° C. for 20 minutes and at room temperature for 20 minutes. The reaction mixture was diluted with ethyl acetate and was washed respectively with water and an aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 3-(4-propoxyphenyl)propyl methanesulfonate (1.02 g) as a colorless oil. was washed respectively with water an aqueous saturated solution of sodium chloride, and the organic layer was dried with anhydrous magnesium sulfate The resulting organic layer was evaporated under reduced pressure to remove the solvent

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

Procedure: A mixture of 3-(4-hydroxyphenyl)-1-propanol (1.33 g), 1-bromopropane (1.2 ml) and potassium carbonate (2.25 g) and acetone (100 ml) was heated at reflux for 2 days. After concentration under reduced pressure, the residue was mixed with water and was extracted with ethyl acetate. The organic layer was washed with a 1 N aqueous solution of sodium hydroxide and an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain 3-(4-propoxyphenyl)-1-propanol (1.61 g) as a colorless oily substance. was heated at reflux for 2 days After concentration under reduced pressure the residue was mixed with water was extracted with ethyl acetate The organic layer was washed with a 1 N aqueous solution of sodium hydroxide an aqueous saturated solution of sodium chloride, and was dried with magnesium sulfate The resulting organic layer was evaporated under reduced pressure to remove the solvent