Sulfuric Acid → 2-Methyloctanoic acid

Participants

Reaction Steps

To 21.2 g (147 mmol) of (-)-2-methyloctanol were added 330 ml of water and 46.4 g of concentrated sulfuric acid with stirring to form an emulsion. To this emulsion was added dropwise 63.4 g (401 mmol) of potassium permanganate over 7 hours. The reaction liquid was added with 51.5 g of sodium hydrogen sulfite, 70 ml of ice water and 200 ml of ether and poured into 270 ml of ice water. After the separation of two layers, the reaction product was extracted from water layer with ether and further with a 10% aqueous solution of sodium hydroxide, which was added with ice and further with concentrated sulfuric acid to adjust pH to not more than 1. The reaction product was extracted from the water layer with chloroform, washed with water, dried on magnesium sulfate and filtered off, and then the filtrate was concentrated and distilled under a reduced pressure to obtain 16.5 g (yield 71%) of a colorless and transparent liquid of (+)-2 -methyloctanoic acid.

Provenance & Evidence