Butyl isocyanate → 4-Chloro-4'-(N-butyl-carbamoyloxy)-alpha-ethyl-benzhydrol

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Reaction Steps

7.9 g. of 4-chloro-4'-hydroxy-α-ethyl-benzhydrol, 3.3 g. of n-butyl-isocyanate and 0.3 ml. of triethyl amine are dissolved in 40 ml. of dry tetrahydrofurane under stirring at 25° C., and the solution is allowed to stand at this temperature for 20 hours. When the reaction is complete, tetrahydrofurane is distilled off under reduced pressure, the residue is taken up in ether, the ethereal solution is shaken with a 5% aqueous sodium hydroxide solution and washed to neutral with water. The organic phase is dried over anhydrous magnesium sulfate, filtered and ether is distilled off in vacuo. Crystallization of the residue from a mixture of n-hexane and ethyl acetate yields 9.3 g. of the named compound, which melts at 78° to 79° C.

Provenance & Evidence