Guaiacol → 2H-1,3-Benzoxazine, 3,4-dihydro-3-(2-(4-chlorophenyl)ethyl)-8-methoxy-

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Reaction Steps

To 20 ml. of dioxane are dissolved 5 g. of orthomethoxyphenol, 5 g. of para-formaldehyde and 12.6 g. of para-chlorophenethylamine. The solution is heated on reflux for 9.5 hours and distilled to remove the solvent. The residue is purified by column chromatography on silica gel with a mixture of acetone and benezene (1:4). Recrystallization of the resultant crude crystals from methanol yields 3-(4-chlorophenethyl)-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine as colorless needles melting at 87-88° C. Yield: 4 g.

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