Sulfuric Acid → 4-Cyanobenzaldehyde

Participants

Reaction Steps

13.2 g of p-cyanobenzylamine and 300 ml of t-butyl alcohol were mixed and 11.9 g of t-butyl hypochlorite was added dropwise at 50° C. over 30 minutes while stirring. After cooling the mixture to room temperature, 12.3 g of potassium t-butoxide was added and stirred at 60° C. for 3 hours. After cooling the mixture to room temperature, 60 g of 10% by weight sulfuric acid was added dropwise over 1 hour and the mixture was stirred for additional 1 hour. The reaction mixture was adjusted to pH 6 by addition of sodium acetate and the solvent was distilled off under reduced pressure. The residue was extracted with toluene and the toluene layer was washed with water. After distilling off the toluene, evaporation under reduced pressure (135° C./15 mmHg) afforded 7.3 g (yield: 56%) of p-cyanobenzaldehyde. The obtained p-cyanobenzaldehyde had a purity of 98% by the analysis of high performance liquid chromatography.

Provenance & Evidence