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Hydroxyaryl methylcarbamates are produced by the monocarbamoylation of the corresponding hydroquinones, which are prepared by persulfate oxidation of the respective phenol, forming a 4hydroxyaryl sulfate, followed by acid hydrolysis. 2 -Isopropoxy -5 -hydroxyphenyl methylcarbamate forms in the following reaction sequence which is designed to produce the proper isomeric configuration: 2-benzyloxyphenol; potassium 3-benzyloxy-4hydroxyphenyl sulfate; 3-benzyloxy-4-isopropoxyphenyl methylcarbamate; 3-hydroxy-4-isopropoxyphenyl methylcarbamate and its bismethylcarbamate; 2-isopropoxy-5-hydroxyphenyl methylcarba-mate. Synthesis routes are given for 2-hydroxyphenyl methylcarbamate and 3-(l -hydroxy-1 -methy 1ethyl)phenyl methylcarbamate. To obtain the de-

There is a need for authentic preparations of substituted-aryl W-hydroxymethylcarbamates because there is reason to believe that these compounds are metabolites of the corresponding substituted-aryl W-methylcarbamates. Substituted-aryl W-hydroxymethylcarbamates are formed by catalytic hydrogenolysis of substituted-aryl W-benzyloxymethylcarbamates, prepared by reaction of the corresponding substituted-phenols with benzyloxymethyl isocyanate. This paper gives two methods for the preparation of benzyloxymethyl isocyanate. It also describes the W-benzyloxymethylcarbamates and W-hydroxymethylcarbamates of the following phenols: 2-isopropoxyphenol; 3-isopropylphenol;

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