Phenol → Methyl 2-methyl-4-(phenoxymethyl)benzoate

Participants

Reaction Steps

A mixture of methyl 4-(hydroxymethyl)-2-methylbenzoate (126 mg, 0.7 mmol), phenol (66 mg, 0.7 mmol), triphenylphosphine (275 mg, 1.0 mmol) and tetrahydrofuran (15 mL) was stirred at room temperature for half hour. And then azodicarboxylic acid diisopropyl ester (212 mg, 1.0 mmol) was added. The mixture was stirred at room temperature for 12 hours. The resultant mixture was washed with water (20 mL×2). The organic phase was separated, dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=5:1) to give methyl 2-methyl-4-(phenoxymethyl)benzoate as a colorless oil (66 mg, 37%). 1H NMR (300 MHz, CDCl3): δ 7.92 (d, J=8.4 Hz, 1H), 7.30-7.24 (m, 4H), 6.97-6.94 (m, 3H), 5.06 (s, 2H), 3.88 (s, 3H), 2.61 (s, 3H).

Provenance & Evidence