Hippuric Acid → HCID 18663606, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 10.0 g (37.59 mmol) of 2-phenoxy-4-trifluoromethyl-benzaldehyde, 10.09 g (56.40 mmol) of hippuric acid and 3.70 g (45.10 mmol) of sodium acetate in 38 ml of acetic anhydride is heated at 85° C. for 80 minutes, then cooled to 32° C. 19 ml of water are added and the mixture is heated at 65° C. for 30 minutes. After cooling the mixture to approximately 5° C., 19 ml of concentrated sulfuric acid are added dropwise and the mixture is then heated under reflux (bath: 140° C.) for 2 hours. The brown precipitate that forms on cooling is filtered and washed with 50% acetic acid, washed with water until neutral and dried to yield 7.42 g (24.23 mmol)=65% of 3-trifluoromethyl-dibenz[b,f]oxepine-10-carboxylic acid in the form of beige crystals; melting point: 180° C.; 1H-NMR (CDCl3, 200 MHz): 7.2-7.65 (m, 8H) 8.09 (s, 1H).

Provenance & Evidence