Water → 4-Hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophene

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Reaction Steps

A solution of 20 g (0.13 mol) of 4,5,6,7-tetrahydro-4-oxo-benzo[b]thiophene in 300 ml absolute ethanol was stirred with 5.4 g (0.14 mol) NaBH4 at ambient temperature for 20 hours. Then 200 ml H2O was added and the ethanol was removed under reduced pressure. The resulting mixture was extracted with ether. The combined organic extracts were backwashed with H2O, dried (Na2SO4), filtered, and evaporated under reduced pressure. The resultant colorless solid was triturated with hexane yielding 19.03 g (95%) of product, mp 58°-60° C.

Provenance & Evidence