Sodium Hydroxide → 8-Chloro-10-hydroxy-7-methoxy-10,11-dihydrodibenzo(b,f)thiepine

Participants

Reaction Steps

A solution of sodium borohydride (0.5 g) in water (3.5 ml), containing 0.1 ml of 15% sodium hydroxide solution was slowly added dropwise to a solution of the ketone from the preceding preparation (6.2 g) in a mixture of benzene (40 ml) and ethanol (100 ml). The stirred mixture was refluxed for 3 hours, the volatile components evaporated under diminished pressure, the residue diluted with water and extracted with benzene. A conventional isolation procedure, followed by crystallization of the crude product from ethanol (25 ml), yielding 5.2 g (83%) of 8-chloro-10-hydroxy-7-methoxy-10,11-dihydrodibenzo(b,f)thiepine, m.p. 130°-132° C.

Provenance & Evidence