o-Vanillin → HCID 136387267, compound

Participants

Reaction Steps

5,6,7,8-Tetrahydro-3-methylquinoline (20 ml), o-vanillin (25 g), acetic anhydride (50 ml), and ZnCl2 (1 g) were heated at reflux for 17 hours. The solvent was removed by evaporation and the residue was dissolved in ethyl acetate (100 ml) and acidified with 2N HCl solution. The solid obtained was removed by filtration and the aqueous layer was basified with Na2CO3 and shaken with diethyl ether. A solid was obtained in the ether layer which was removed by filtration. The combined solids were dissolved in 1N sodium hydroxide and the solution was extracted with ethyl acetate. The extracts were dried over MgSO4 and the solvent was removed by evaporation. The crystals obtained were washed with hexane and dried to give the title compound (6 g) m.p. 149°-153° C.

Provenance & Evidence