Phenol → (2S)-2-(phenoxymethyl)oxirane

Participants

Reaction Steps

A solution of phenol (9.4 g, 100 mmol) and (2S)-(+)-glycidyl 3-nitrobenzenesulfonate (25.9 g, 100 mmol) in 500 mL of acetone was treated with 3 equivalents of potassium carbonate (41.5 g, 300 mmol) and stirred at reflux for 1 day. The suspension was cooled to ambient temperature; the solid was filtered; and the filtrate was concentrated to dryness. The residue was partitioned between methylene chloride and water. The aqueous layer was extracted with CH2Cl2. The organic layers were combined and dried over MgSO4 and concentrated to give the title compound (15.0 g, 99%) as an orange oil; 1H NMR (300 MHz, CDCl3) δ 2.76 (dd, J=4.9, 2.6 Hz, 1H), 2.90 (dd, J=4.9, 4.9 Hz, 1H), 3.30-3.40 (m, 1H), 3.95 (dd, J=11.0, 5.4 Hz, 1H), 4.18 (dd, J=11.0, 3.0 Hz, 1H), 6.85-7.00 (m, 3H), 7.25-7.35 (m, 2H); MS (ES) m/z: 151.0 (MH+).

Provenance & Evidence