Protocatechuic Acid → Pentyl 3,4-dipentyloxybenzoate

Participants

Reaction Conditions

Reaction Steps

3,4-Dihydroxybenzoic acid (462 mg, 3 mmol) was dissolved in DMF (10 ml). Potassium carbonate (3.73 g, 27 mmol, 9 eq) and 1-bromopentane (1.70 ml, 13.5 mmol, 4.5 eq) were successively added to this solution at room temperature, and the mixture was stirred at 110° C. for 24 hours. This reaction mixture was filtered, and the residual potassium carbonate was washed with ethyl acetate (50 ml). The filtrate was washed with water (15 ml×3) and saturated brine (15 ml). The organic layer was dried over anhydrous sodium sulfate. After the drying agent was filtered off; the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (heaxane/ethyl acetate=95/5) to give pentyl 3,4-dipentyloxybenzoate (912 mg, 83%).

Provenance & Evidence