Hydrochloric Acid → 2-Methyloctanoic acid

HRID 2372241Notes

Reaction equation

HRID 2372241 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 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.

Workup

  1. additionwas added dropwise over 7.3 hours
  2. customat 21°-28° C
  3. customThe thus obtained reaction mixture
  4. additionwas added
  5. extractionthe resulting product was extracted with ether and further with a 10% aqueous solution of sodium hydroxide
  6. additionThe extract was added with hydrochloric acid
  7. extractionagain extracted with chloroform
  8. customThe thus obtained
  9. extractionextract
  10. washwas washed with water
  11. customdried
  12. concentrationconcentrated
  13. distillationdistilled under a reduced pressure (0.28 mmHg, 91°-94° C.)

Sources & evidence

ORD record
ord-1a2c0e3963534904a053fb18c043834c
Source dataset
uspto-grants-1992_03
Patent number
US05098602

Reaction notes

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