Water → 12-Oxododecanoic acid

Participants

Reaction Steps

A 2.40 g (0.008 mol) sample of the acid was placed in a 250 mL Erlenmeyer flask and dissolved with 18 mL water and 9 mL tertiary butyl alcohol. The mixture was stirred continuously for homogeneity, followed by addition of 1.95 g (0.0086 mol) periodic acid in one portion. The reaction mixture was then stirred for 5 hours, after which 150 mL ice-cold water was added. The mixture was stirred for another 30 minutes and the resulting solid was vacuum-filtered to give crude 12-oxododecanoic acid. The acid was washed, then recrystallized with light petroleum (bp 35°-60° C.) to give 1.22 g 12-oxododecanoic acid (73% yield, m.p. 53°-54° C.) and hexanal. There was no attempt to isolate the hexanal.

Provenance & Evidence