Sodium Hydroxide → HCID 22915485, compound

Participants

Reaction Steps

A mixture of 3-(3-phenylphenoxy)propionic acid (0.27 g, 1.1 mmol) and excess thionyl chloride was heated at reflux for 30 minutes. The mixture was cooled to ambient temperature and concentrated in vacuo. The residue was azeotroped three times with ethyl ether, and then was taken up in THF (30 mL). To the acid chloride solution was added aqueous hydroxylamine (3.34 mmol; prepared by adding 2.8 mL of aqueous 50% NaOH to a solution in 5 mL water of hydroxylamine hydrochloride) and the reaction mixture was stirred for 4 hours. The reaction mixture was quenched with 1:1 dichloromethane-saturated aqueous NH4Cl. The aqueous phase was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was taken up in ethyl ether and left standing at -30° C. for 3 days. The resulting crystals were collected to give 3-(3-phenylphenoxy)propanohydroxamic acid. mp 113°-116° C. 1H NMR (DMSO-d6) δ 10.58 (s, 1H), 8.68-8.63 (d, 1H, J=1.5 Hz), 7.67-7.65 (d, 2H, J=7 Hz), 7.48-7.43 (t, 2H, J=7.7 Hz), 7.38-7.34 (t, 2H, J=7.7 Hz), 7.24-7.21 (d, 1H, J=7.4 Hz), 7.15 (m, 1H), 6.94-6.90 (dd, 1H, J=3, 7 Hz), 4.28-4.24 (t, 2H, J=6 Hz), 2.47-2.43 (t, 2H, J=6 Hz). MS (DCI/NH3) 275 (M+NH4)+. Anal. Calcd for C15H15NO3 ·0.25H2O: C, 68.82; H, 55.96; N, 5.35. Found: C, 68.92; H, 5.87; N, 5.33.

Provenance & Evidence