Hydrochloric Acid → 4-(5-(4-(Pentyloxy)phenyl)-3-isoxazolyl)benzoic acid

Participants

Reaction Steps

To 92 mg (0.26 mmol) methyl 4-[3-(4-pentyloxyphenyl)-3-oxopropanoyl]benzoate in 10 mL ethanol was added 146 mg (3.63 mmol) sodium hydroxide and 500 mg (7.25 mmol) hydroxylamine hydrochloride in 2 mL water. The solution was refluxed for 7 h. After cooling to room temperature, 1 M hydrochloric acid was added and the precipitate formed was filtered off and washed with water. Upon drying, the product was obtained as a white solid (22 mg, 0.06 mmol, 23%). 1H NMR (D6-acetone, 500 MHz): δ=8.18 (d, 2H, J=8.6 Hz), 8.06 (d, 2H, J=8.5 Hz), 7.89 (d, 2H, J=8.6 Hz), 7.30 (s, 1H), 7.11 (d, 2H, J=8.6 Hz), 4.08 (t, 2H, J=7.3 Hz), 1.82 (m, 2H), 1.47 (m, 4H), 0.93 (t, 3H, J=7.3 Hz). HPLC: 4.641 min.

Provenance & Evidence