Water → HCID 19977493, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1:1 water and tert-butanol (10 mL), AD-mix-α (Aldrich, 1.4 g) was added and the mixture stirred for 0.1 h. The mixture had two layers; the lower layer was yellow in color. To this mixture, ethyl-4-acetylamino-3-allylbenzoate (0.1 g, 0.0004 mol) was added in one portion and stirred at room temperature for 48 h. The reaction mixture was cooled to 0° C. and sodium sulphite (1.5 g, 0.0119 mol) was added. The reaction was stirred at 0° C. for 0.3 h and then at room temperature for 0.5 h. It was extracted with ethyl acetate (3×15 mL), the combined organic layers were dried over sodium sulphate, filtered, and concentrated. The residue was passed through a column of silica gel eluting first with 1:1 ethyl acetate:hexane to recover the starting material, and then with pure ethyl acetate to give 0.075 g (66%) of ethyl-4-acetylamino-3-(2',3'-dihydroxypropyl)benzoate (isomer A) as a white powder, mp 114°-116° C. The optical rotation of this solid was 0° at 589 nm.

Provenance & Evidence