Guaiacol → HCID 12268981, compound

Participants

Reaction Steps

To 120 ml. of dioxane are added 5 g. of ortho-methoxyphenol, 9 ml. of 37% formalin and 7.56 g. of ortho-chlorophenethylamine. The mixture is heated on reflux for 3 hours and distilled to remove the solvent. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4). The resultant oil is cooled to be solidified. Recrystallization from methanol yields 3-(2-chlorophenethyl)-8-methoxy-3,4-dihydro-2H-1,3-benzoxazine as colorless needles melting at 79°-81° C. Yield: 6 g.

Provenance & Evidence