Formaldehyde → 3,5-Di-tert-butyl-4-hydroxybenzaldehyde

Participants

Reaction Steps

A 500 ml reaction flask fitted with a mechanical stirrer, heating mantle, thermometer and water-cooled condenser was charged with 166 ml of glacial acetic acid and 34 ml of water. To the stirred solution were added 61.7 g (0.8 mole) of ammonium acetate, 12 g of paraformaldehyde (0.4 mole equivalent of formaldehyde) and 20.6 g (0.1 mole) of 2,6-ditert.butylphenol. The mixture was refluxed (111°-12°) for 6 hours. After cooling to ambient temperature, the mixture was poured on a vacuum filter and the cake was washed with water. After drying, there was obtained 13.6 g (58%) of impure 3,5-ditert.butyl-4-hydroxybenzaldehyde, m.p. 174°-80°. Following recrystallization from 2-propanol, the yellow crystalline product melted at 188°-90°.

Provenance & Evidence