Water → 3,3-Dimethyl-5-oxohexanoic acid

Participants

Reaction Steps

There was added 0.15 part of solid ruthenium oxide to a solution of 2.8 parts of isophorone and 2.5 parts of sodium periodate in about 200 parts of acetone to 40 parts of water. The resulting yellow solution was stirred while 5 parts of sodium periodate, 50 parts of water and 20 parts of acetone was added over an hour. The resulting suspension was stirred 48 hours at room temperature then filtered through Celite. The resulting filtrate was then extracted with methylene chloride. The organic phase was extracted with CHCl3. Acidification of the base washings provided 2 parts, or a 63% yield of 5-keto-3,3-dimethylhexanoic acid.

Provenance & Evidence