Triethylamine → 2,6-Dimethyl-3-(2-chloroethyl)-5,6-dihydro-1,4-oxathiin

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Reaction Steps

A mixture of 0.1 mole (15.4 g.) 3,5-dichloro-2-pentanone, and 0.1 mole (9.2 g.) 1-mercapto-2-propanol was stirred in 100 ml toluene; 0.1 mole (10.4 g.) triethylamine was added dropwise. The mixture was stirred at room temperature overnight, then washed with dilute hydrochloric acid and reluxed with 0.5 g. PTSA, using a Dean-Stark trap to remove water for about 7 hours. The PTSA solution was washed with sodium bicarbonate, dried over magnesium sulfate and the solvent was removed. The product was distilled; bp 80°-82°/0.1 mm. Yield 47%.

Provenance & Evidence