Ethylene Glycol → HCID 57234343, compound

Participants

Reaction Steps

To a solution of 9.4 g (0.045 mol) of ethanethioic acid S-(2-oxo-1-phenylpropyl)ester and 3.1 g (0.05 mol) of ethylene glycol in 125 ml of benzene was added 1.0 g p-toluenesulfonic acid. The mixture was then heated at reflux over a period of 10 hours while the water formed was removed with the aid of a Dean-Stark trap. The mixture was concentrated under reduced pressure and the residue 11.0 g was chromatographed on 150 g of silica gel. The column was eluted with methylene chloride and fractions 6-20 were collected. Removal of the solvent gave 7.6 g (67%) of rac.-ethanethioic acid-[(2-methyl-1,3-dioxolan-2-yl)phenylmethyl]ester. A sample of this compound was crystallized from pet. ether, mp 49°-52°.

Provenance & Evidence