Hydrochloric Acid → HCID 15124027, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-methyl-4-hydroxy-5-tert-butylbenzofuran-7-p-chlorobenzoylbenzofuran-2-carboxylic acid, compound 18 (0.281 g, 0.73 mmol), copper (0.046 g, 0.73 mmol), and quinoline (1 mL) was heated to 160° C. until gas evolution had ceased. The reaction mixture was allowed to cool and poured into 2N HCl (25 mL). Ethyl acetate (25 mL) was added and the mixture was filtered through a pad of celite. The layers were separated and the aqueous layer reextracted with ethyl acetate (2×20 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Flash chromatography using 10% ethyl acetate as eluant afforded 3-methyl-4-hydroxy-5-tert-butyl-7-p-chlorobenzoylbenzofuran, compound 19 as an oil which solidified on standing. 1H NMR d 1.50 (9H, s), 2.50 (3H, d, J=2 Hz), 5.79 (1H, s), 7.30 (1H, s), 7.46 (2H, d, J= 8 Hz), 7.66 (1H, s), 7.79 (2H, d, J=8 Hz).

Provenance & Evidence