4-[4-(3-Hydroxypropyl)phenoxy]butanoic acid → HCID 54240155, compound

Participants

Reaction Steps

A 1.19 g (5.00 mmol) sample of 4-[4-(3-hydroxypropyl)phenoxy]butanoic acid is dissolved with stirring in 250 mL of methylene dichloride. Next, 3.77 g (17.49 mmol) of pyridinium chlorochromate is added, the mixture is stirred for 4 hours, and then filtered through a celite pad. The reaction mixture is then diluted with an equal volume of ether, precipitating out salts. This mixture is then filtered through a silica gel pad, and the filtrate evaporated, giving a brown solid. The solid is recrystallized from an ether-hexane mixture producing 0.21 (18%) of 4-[4-(3-oxopropyl)phenoxy]butanoic acid as off-white crystals: m.p. 100°-03° C.; IR (KBr) 1715 cm-1 ; 1H-NMR (CDCl3) is consistent with the desired product; MS (CI) m/e 237 (M+ +H). Analysis calculated. for C13H16O4 : C, 66.09; H, 6.83; O, 27.09. Found: C, 65.91; H, 6.72; O, 27.35.

Provenance & Evidence