Terephthalaldehyde → 4-(Hydroxymethyl)benzaldehyde

Participants

Reaction Steps

Terephthalaldehyde (25.0 g) was suspended in water (20 ml) and ethanol (80 ml). Pd/C (220 mg) was added to the suspension and then hydrogen gas (4.3 l ) was introduced. The catalyst was removed by filtration and the filtrate was concentrated to give p-hydroxymethylbenzaldehyde (25.2 g). The product was dissolved in toluene (100 ml) and 48% HBr (50 ml) and the solution was refluxed for 2 hours. The reaction mixture was poured into iced water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated saline and dried, and then the solvent was removed by evaporation under reduced pressure. The residue was recrystallized from n-hexane to give colorless needles (37.5 g, yield: 82%). mp 97.5°-98.0° C.

Provenance & Evidence