Acetone → (S)-3-Methylheptanoic acid

Participants

Reaction Steps

To 10 g. of 3-(S)-methyl-1-heptanol in 175 ml. of acetone was added over 45 minutes 90 ml. of Jones reagent dropwise at 15°-20° C. After 15 minutes, 15 ml. of isopropanol was added and stirring continued for 30 minutes. The reaction was poured into water and the product extracted with ether. The extracts were combined, washed with water, a sodium bisulfite solution and a brine solution and dried over magnesium sulfate. Removal of the solvent gave 10 g. of the product as a liquid, b.p. 84°-88° C./0.4 torr, [alpha]D =-4.46 (CH3OH C=0.105 g/ml.).

Provenance & Evidence