Water → 4-Geranyloxybenzoic acid

Participants

Reaction Steps

Methyl 4-hydroxybenzoate (7.6 g), geranyl bromide (10.9 g), and potassium carbonate (13.8 g) were refluxed in acetone (80 ml) with stirring for 6 hours. The reaction mixture, with water added thereto, was extracted with chloroform. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was dissolved in methanol (50 ml) and the resulting mixture, with potassium hydroxide (3.9 g) and water (10 ml) added thereto, was stirred overnight at room temperature. The reaction mixture was neutralized with hydrochloric acid and then extracted with chloroform. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The resulting solid was recrystallized from n-hexane/ethanol to yield 9.8 g of the aimed compound.

Provenance & Evidence