Hydrochloric Acid → 2-Methyloctanoic acid

Participants

Reaction Steps

After 46.4 g of concentrated sulfuric acid and 21.2 g (147 mmol) of (-)-2-methyloctanol were added to 330 ml of water, 63.4 g (401 mmol) of potassium permanganate was added dropwise over 7.3 hours while holding a reaction temperature at 21°-28° C. The thus obtained reaction mixture was poured into 270 ml of ice water, and 52 g of sodium bisulfite was added thereto. After pH was adjusted to not more than 1 with hydrochloric acid, the resulting product was extracted with ether and further with a 10% aqueous solution of sodium hydroxide. The extract was added with hydrochloric acid to adjust pH to not more than 1 and again extracted with chloroform. The thus obtained extract was washed with water, dried, concentrated and then distilled under a reduced pressure (0.28 mmHg, 91°-94° C.) to obtain 15.3 g (yield: 64%) of (+)-2-methyl octanoic acid.

Provenance & Evidence