Diethyl terephthalate → Terephthalic Acid

Participants

Reaction Conditions

Reaction Steps

Phenoxanol in the amount of 35.80 g (0.201 mol) and diethyl p-phthalate in the amount of 13.00 g (0.067 mol) were combined in a 250 ml flask fitted with a heating mantel, take-off condenser, internal thermometer, and argon inlet. Sodium methoxide in the amount of 380 mg (6.70 mmol) was added to the contents of the flask. The mixture was heated to 100° C. for 5 h during which time it became very thick. The mixture was filtered with dichloromethane, concentrated by rotary evaporation, and stripped by Kugelrohr distillation to yield an oil. The oil was purified by column chromatography on silica gel eluting with a 2% solution of ethyl acetate in hexanes to yield a colorless oil that crystallized on standing. Purity of the product was determined by thin layer chromatography and the structure confirmed by 1H and 13C NMR.

Provenance & Evidence