Hexamethylenetetramine → 2,3,4,5-Tetramethoxy-6-methylbenzaldehyde

Participants

Reaction Steps

To a solution of 1,2,3,4-tetramethoxy-5-methylbenzene (34.3 g, 162 mmol) in trifluoroacetic acid (200 ml) was added hexamethylenetetramine (25.0 g, 178 mmol), and the solution was heated under reflux for 3 hours. The solvent was distilled off under reduced pressure. Water (200 ml) was added to the residue which was then heated under reflux for one hour, neutralized with 3N sodium hydroxide and extracted with ethyl acetate (200 ml×3), and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography to give 34.9 g of the title compound.

Provenance & Evidence