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

Participants

Reaction Steps

To 20 ml. of dioxane are added 5 g. of ortho-methoxyphenol, 9 ml. of 37 % formalin and 6.7 g. of para-methoxyphenethylamine. The mixture is heated on reflux for 4 hours and concentrated to dryness under reduced pressure. The residue is purified by column chromatography on silica gel with a mixture of acetone and benzene (1:4). The resultant oily substance is left standing at cool place for one month to be solidified. Recrystallization from petroleum ether yields 8-methoxy-3-(4-methoxyphenethyl)-3,4-dihydro-2H-1,3-benzoxazine as melting at 69°-70° C.

Provenance & Evidence