Phenol → 3,5-Di-tert-butylsalicylaldehyde

Participants

Reaction Steps

2,4-di-t-butylphenol (75 g, 0.36 mole) was dissolved in 200 ml absolute ethanol in a 1 L round bottom flask equipped with a water-cooled condenser. Sodium hydroxide (82 g, 2.0 moles) was dissolved in 80 ml water and added while still hot to the solution of phenol. Chloroform (156 g, 1.31 mole) was added in 2 ml portions over a 45-minute period. The resulting yellow-brown mixture was stirred 1 hour while cooling to ambient temperature. The mixture was diluted with 500 ml of 1M sulfuric acid and extracted with 200 ml of dichloromethane. The organic layer was isolated in a separatory funnel and dried over anhydrous magnesium sulfate. The mixture was filtered and rotoevaporated to a thick syrup. The yield was 33%. The IR spectrum of the crude product showed the characteristic aldehyde carbonyl (C=O) stretching frequency at 1648 cm-1. The product was used without further purification.

Provenance & Evidence