Hydrochloric Acid → 2-Methyloctanoic acid

HRID 846550Notes

Reaction equation

HRID 846550 reaction equation
S(=O)(=O)(O)O.[CH3:6][CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][OH:9].[Mn]([O-])(=O)(=O)=[O:17].[K+].S([O-])(O)=O.[Na+].Cl>O>[CH3:6][CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:8]([OH:17])=[O:9]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 1024952-MethyloctanolHCID 516875Potassium PermanganateHCID 23665763Sodium Bisulfite

Product 1

HCID 942512-Methyloctanoic acidYield 65.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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 the reaction temperature was held at 21°~28° C. The thus obtained reaction mixture was poured into 270 ml of ice water, added with 52 g of sodium hydrogen sulfite, adjusted to pH of not more than 1 with hydrochloric acid, extracted with ether and then extracted with a 10% aqueous solution of sodium hydroxide. This extract was added with hydrochloric acid to adjust pH to not more than 1 and again extracted with chloroform. The extract was washed with water, dried, concentrated and distilled under a reduced pressure (0.28 mmHg, 91°~94° C.) to obtain 15.3 g (yield 64%) of (+)-2-methyl octanoic acid.

Workup

  1. additionwas added dropwise over 7.3 hours while the reaction temperature
  2. customwas held at 21°~28° C
  3. customThe thus obtained reaction mixture
  4. extractionextracted with ether
  5. extractionextracted with a 10% aqueous solution of sodium hydroxide
  6. additionThis extract was added with hydrochloric acid
  7. extractionagain extracted with chloroform
  8. washThe extract was washed with water
  9. customdried
  10. concentrationconcentrated
  11. distillationdistilled under a reduced pressure (0.28 mmHg, 91°~94° C.)

Sources & evidence

ORD record
ord-266c8bf2c1cd44039b1782665a770f50
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

Loading…