1-Bromopentane → HCID 19363254, compound

Participants

Reaction Conditions

Reaction Steps

3-Hydroxy-4-methoxybenzoic acid (9.6 g, 0.057 mol) was dissolved in DMF (90 ml), and to this solution were successively added 1-bromopentane (25.9 g, 0.17 mol, 3.0 eq) and anhydrous potassium carbonate (47.4 g, 0.34 mol, 6.0 eq). The mixture was stirred under heating at 90° C. for 3 hours. This reaction mixture was cooled to room temperature, and anhydrous potassium carbonate was filtered off. Water (200 ml) was added to the filtrate, and the mixture was extracted twice with ethyl acetate (200 ml). The organic layers were combined, washed with saturated brine (300 ml) and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (n-hexane/ethyl acetate=15/1-10/1) to give pentyl 4-methoxy-3-pentyloxybenzoate (17.4 g, 98.8%) as a colorless oil.

Provenance & Evidence