Potassium Hydroxide → (3-Thien-3-ylphenyl)methanol

Participants

Reaction Steps

To 3.3 g (0.014 mol) of 3-(3-thienyl)phenylmethyl acetate was added with stirring a solution of 1.4 g (0.021 mol) of potassium hydroxide in 100 mL of methanol. The reaction mixture was stirred at ambient temperature for 19 hours. The volume of the reaction mixture was reduced to to 30 mL by concentration under reduced pressure. The concentrate was placed in a separatory funnel, and 100 mL of a saturated aqueous solution of sodium chloride was added. The mixture was extracted with five portions of 60 mL each of methylene chloride. The extracts were combined and washed with 200 mL of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a residual oil. The oil was subjected to column chromatography on silica gel, eluting with toluene:pentane (3:2). The appropriate fractions were combined to give 2.8 g of 3-(3-thienyl)phenylmethanol.

Provenance & Evidence