Hexamethylenetetramine → 3-tert-Butyl-4-hydroxy-5-methylbenzaldehyde

Participants

Reaction Steps

Under a nitrogen atmosphere, 76.65 g of 2-(1,1-dimethylethyl)-6-methylphenol (Aldrich), 65.42 g of hexamethylenetetramine and 700 ml of trifluoroacetic acid were stirred at reflux temperature for about 24 hours. The reaction solution was allowed to cool and the liquid removed by evaporation. The resulting residue was taken up in 1500 ml of water and 1000 ml of chloroform and then neutralized to pH 7 with solid sodium carbonate. The resultant layers were separated and the aqueous layer was washed with chloroform. The organic layer was combined with the chloroform wash and the resulting solution was washed with water, then dried over sodium sulfate overnight. After removal of the sodium sulfate the chloroform was evaporated. The resultant residue was taken up in 375 ml of toluene, heated on a steam bath and then allowed to cool to room temperature overnight. Subsequent workup gave 28.3 g of the subtitled intermediate.

Provenance & Evidence