Hydrochloric Acid → 4-(Cyclopropylmethoxy)-2-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

A suspension of (bromomethyl)cyclopropane (20.0 g, 148 mmol), 4-hydroxy-2-methylbenzoic acid (10.1 g, 66.4 mmol) and potassium carbonate (22.0 g, 159 mmol) in DMF (150 mL) was stirred at 60° C. overnight. Ethyl acetate was added thereto, the mixture was left standing, and the resulting precipitate was removed by filtration. The filtrate was concentrated under reduced pressure, water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. To the obtained residue were added methanol (50 mL), water (50 mL), THF (100 mL) and lithium hydroxide monohydrate (3.00 g, 71.4 mmol), and the mixture was stirred at 50° C. for 3 hr. After being allowed to cool to room temperature, the mixture was acidified with 1N hydrochloric acid, and the resulting precipitate was collected by filtration, washed with water, and dried to give the title compound (13.5 g, yield 92%) as a white solid.

Provenance & Evidence