Methylparaben → HCID 60778955, compound

Participants

Reaction Steps

To a solution of tetrahydrofuran-3-ylmethanol (21.89 g), methyl 4-hydroxybenzoate (33.5 g) and triphenylphosphine (64.5 g) in tetrahydrofuran (400 mL) was slowly added dropwise a solution (120 mL, 40% toluene solution) of diethyl azodicarboxylate in toluene at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and triphenylphosphine oxide was precipitated from ethyl acetate-hexane. The mixture was filtered through a glass filter to remove triphenylphosphine oxide, and the filtrate was concentrated. The residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=90:10 (volume ratio)→hexane:ethyl acetate=40:10] to give a colorless oil. The obtained colorless oil was dissolved in tetrahydrofuran (200 mL) and methanol (100 mL), 8N aqueous sodium hydroxide solution (100 mL) was added, and the mixture was stirred with heating at 80° C. for 2 hr. The reaction solution was concentrated, cooled to 0° C., and neutralized with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (23 g, yield 48%) as colorless crystals.

Provenance & Evidence