5-(Benzyloxy)pentan-1-ol → 5-(Benzyloxy)pentanoic acid

Participants

Reaction Steps

Jones reagent was added dropwise to an ice cooled solution of 5-benzyloxy-pentan-1-ol 28 (5 g, 25.74 mmol) in acetone (170 ml). Addition of the Jones reagent was stopped when the acetone solution acquired a persistent yellow color with the concurrent formation of green chlomium salts. The mixture was filtered and concentrated in vacuo to give an oily crude product that was purified by a flash chromatography (EtOAc/hexanes, 1:3) to give compound 29 (4.98 g, 93%) as a colorless oil: TLC Rf=0.68 (silica gel, 50% EtOAc/hexanes); 1H NMR (400 MHz, CDCl3) δ 7.35-7.31 (m, 5H), 4.502 (s, 2H), 3.51-3.47 (t, 3J=6 Hz, 2H), 2.41-2.36 (t, 3J=6.8 Hz, 2H), 1.79-1.64 (m, 4H); 13C NMR (75 MHz, CDCl3) δ 179.713, 138.651, 128.609, 127.870, 127.795, 73.158, 69.968, 33.915, 29.243, 21.749; HRMS calcd for C12H16O3+Na+ 231.0997; found 231.0992 [M+Na+].

Provenance & Evidence