Sulfuric Acid → 2-Methyloctanoic acid

To 21.2 g (147 mmol) of (-)-2-methyloctanol were added an aqueous solution of 330 ml of water and 46.4 g of concentrated sulfuric acid, which was stirred to form an emulsion. To this emulsion was added dropwise 63.4 g (401 mmol) of potassium permaganate over 7 hours. Then, the reaction mixture was added with 51.5 g of sodium bisulfite and poured into 270 ml of ice water together with 70 ml of ice water and 200 ml of ether. After the separation into two layers, the reaction product was extracted from the aqueous layer with ether, which was further extracted with a 10% aqueous solution of sodium hydroxide, added with ice and further with a concentrated hydrochloric acid to adjust the pH to not more than 1. Thereafter, the extraction with chloroform on the aqueous layer was performed, which was washed with water, dried on magnesium sulfate and filtered. 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-methyl octanoic acid.

1. customto form an emulsion
2. customAfter the separation into two layers
3. extractionthe reaction product was extracted from the aqueous layer with ether, which
4. extractionwas further extracted with a 10% aqueous solution of sodium hydroxide
5. additionadded with ice and further with a concentrated hydrochloric acid
6. extractionThereafter, the extraction with chloroform on the aqueous layer
7. washwhich was washed with water
8. customdried on magnesium sulfate
9. filtrationfiltered
10. concentrationThe filtrate was concentrated
11. distillationdistilled under a reduced pressure

ORD record

ord-1e78b4f5fd1b45f48643eb92f64d3672

Source dataset

uspto-grants-1990_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04970023