Water → 1,2-Butanediol diacetate

Participants

Reaction Steps

To the mixture of 0.48 g of optically active 1,2-butanediol, 5 ml of toluene and 2.5 ml of pyridine, 1.7 g of acetyl chloride was added dropwise in an ice bath and stirred for two hours. 10 ml of water and 10 ml of toluene were added to the reaction mixture and stirred. The obtained solution was washed with 2N sodium hydroxide and then with water. The toluene solution was dried over anhydrous magnesium sulfate. Toluene was distilled away from the solution under reduced pressure, the residue was purified with a chromatograph over silica gel, and 1,2-butanediol diacetate was obtained. The obtained compound had a gas chromatographic purity of 98.9%. It showed a specific rotation of [α]D28 =-12.2° C. (c=1.08, CHCl3). The optical purity of the compound was determined by using a column of optical resolution (Trade name: Chiral Cel OB, produced by Daicel Chemical Industries, Ltd., in Japan). From the peak area of the product, the optical purity was 85% ee.

Provenance & Evidence