Epichlorohydrin → 4-[(2S)-2-OxiranylMethoxy]benzeneacetaMide

Participants

Reaction Conditions

Reaction Steps

p-Hydroxyphenyl acetamide (30.02 g) was dissolved in 106.5 g of water containing sodium hydroxide (9.6 g) and the solution was cooled to 5° C. Epichlorohydrin (18.5 g, 98.9% e.e.) was dropped in the solution over a period of 10 minutes under stirring at the same temperature and the solution was stirred for 24 hours. Sodium hydroxide (2.4 g) was added thereto and the mixture was stirred for 5 hours. Resulting crystals were filtrated by suction, washed with water and dried in vacuo to give crude (S)-1-[p-(carbamoylmethyl)phenoxy]-2,3-epoxypropane (39.8 g). The optical purity of it was 91.2% e.e. by measurement of Chiral column OD (Daisel Chemical Industries Ltd.).

Provenance & Evidence