Methanol → 3-methylthio-5H-dibenzo[a,d]cyclohepten-5-ol

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Reaction Steps

3-Methylmercapto-5H-dibenzo[a,d]cyclohepten-5-one, 27.9 g. (0.11 mole), is dissolved in 500 ml. of methanol. The solution is stirred and heated to refluxing while a solution of 14.9 g. (0.276 mole) of potassium borohydride in 150 ml. of water containing 0.2 ml. of 10 N. sodium hydroxide is added dropwise. After stirring at reflux for 2 hours, the solution is chilled and the precipitated product collected and washed with methanol yielding, typically, 27 g. (96%). An analytical sample melts at 117°-118.5°C. after repeated recrystallizations from methanol.

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