Potassium Carbonate → 92642-95-0

Participants

Reaction Steps

To a stirred mixture of 41.6 g of ethyl 2,3-dibromopropionate, 400 ml of dry acetone and 11.1 g of potassium carbonate, there was added dropwise at 27° C. a solution of 19.5 g of o-mercaptophenol in 75 ml of acetone. After the addition was complete, the reaction mixture was stirred at room temperature for 10 minutes and an additional 50.9 g of potassium carbonate was added. The reaction mixture then was refluxed for 2 hours, and allowed to stand overnight at room temperature. The mixture was filtered and the solid was washed with acetone, the washings being added to the filtrate. The acetone was stripped to leave a liquid, which was taken up in methylene chloride. The resulting solution was washed with water and dried (MgSO4), and the solvent was stripped. The resulting liquid was dry column chromatographed through silica gel, using a 4:16:80 by volume mixture of tetrahydrofuran, ethyl acetate and hexane (Solvent No. 2) as eluent, to give the ethyl ester of 2,3-dihydro-1,4-benzoxathiin-2-carboxylic acid (1A), as a light yellow liquid, boiling point not determined.

Provenance & Evidence