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

Participants

Reaction Steps

To a reaction vessel were added (S)-epichlorohydrin (99% ee, 30.0 g, 0.32 mol), benzyltrimethylammonium chloride (0.80 g), toluene (70 ml) and water (70 ml), and the mixture was cooled with ice. After addition of phenol (20.3 g, 0.22 mol), thereto 24% aqueous NaOH solution (54.0 g, 0.33 mol) was dropped in a period of one hour under stirring. The mixture was stirred for 30 minutes under ice-cooling and then for 39 hours at room temperature. After the reaction the aqueous layer was removed and the organic layer was neutralized with 5% aqueous HCl solution (70 ml) and washed with water (40 ml). After removal of toluene, the residue was distilled to give objective (R)-glycidylphenyl ether (27.0 g, yield 83%, optical purity 98% ee) as a colorless liquid.

Provenance & Evidence