Sulfuric Acid → 2-Methyloctanoic acid

HRID 846557Notes

Reaction equation

HRID 846557 reaction equation
[CH3:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][OH:4].S(=O)(=O)(O)[OH:12].[Mn]([O-])(=O)(=O)=O.[K+].S([O-])(O)=O.[Na+]>CCOCC.O>[CH3:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:3]([OH:12])=[O:4]

Participants

7

Reactant 4

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

Product 1

HCID 942512-Methyloctanoic acidYield 71%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  1. customto form an emulsion
  2. customThe reaction liquid
  3. customAfter the separation of two layers
  4. extractionthe reaction product was extracted from water layer with ether and further with a 10% aqueous solution of sodium hydroxide, which
  5. additionwas added with ice and further with concentrated sulfuric acid
  6. extractionThe reaction product was extracted from the water layer with chloroform
  7. washwashed with water
  8. customdried on magnesium sulfate
  9. filtrationfiltered off
  10. concentrationthe filtrate was concentrated
  11. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-a55f5f50fa0c4d8295e1b6a702635043
Source dataset
uspto-grants-1992_08
Patent number
US05137653

Reaction notes

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