Benzene → N-Trichloroacryloyl-p-aminobenzoic acid

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Reaction Steps

Trichloroacrylic acid (500 mg, 2.85 mmol; Alpha Chem. Co.) was added to 7 mL of SOCl2 and the mixture was refluxed for 6 h. After cooling, 5 mL of benzene was added and the solvent was concentrated on the rotary evaporator to 1/3 of its original volume. This step was repeated 4 times, until most of SOCl2 was evaporated. Three mL of acetonitrile were added followed by a suspension of 383 mg (2.80 mmol) of p-amino-benzoic acid in 3 mL of acetonitrile. After 30 min of stirring, TLC showed the disappearance of most starting material and the presence of a product with higher Rf value. The product was purified by preparative silica TLC (EtOAC/Hexane/acetic acid, 2:3:0.05) which gave a pure white powder (89% yield); MS (EI) m/z 293 (M+).

Provenance & Evidence