Phenol → (2R)-2-(Phenoxymethyl)oxirane

Participants

Reaction Steps

To a reaction vessel were added (S)-epichlorohydrin (99% ee, 2.64 g, 29 mmol), toluene (6 ml) and water (6 ml), and the mixture was cooled with ice. After adding phenol (1.78 g, 19 mmol), thereto 24% aqueous NaOH solution (4.75 g, 29 mmol) was dropped under stirring over a ten minute period. The mixture was stirred for 30 minutes under ice-cooling and then for 50 hours at room temperature. The aqueous layer was removed and the organic layer was neutralized with 5% HCl and washed with water twice. The solvent was removed to give objective crude (R)-glycidylphenyl ether (1.96 g, yield 69%, optical purity 98% ee) as an oil.

Provenance & Evidence