Sulfuric Acid → 2-Hexyldecanoic acid

HRID 1656657Notes

Reaction equation

HRID 1656657 reaction equation
S(=O)(=O)(O)O.[CH2:6]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][OH:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Mn]([O-])(=O)(=O)=[O:24].[K+]>O.C(Cl)Cl>[CH2:6]([CH:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:13]([OH:24])=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 953372-Hexyl-1-decanolHCID 516875Potassium Permanganate

Product 1

HCID 329122-Hexyldecanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Concentrated sulphuric acid (100 g) was diluted with water (750 ml) and this solution was cooled to room temperature and added to a solution of 2-hexyldecanol (242 g) in methylene chloride (600 ml). The solutions were stirred together beneath a reflux condenser and solid potassium permanganate was added in portions during 5 hours so as to maintain gentle boiling of the methylene chloride. The mixture was filtered to remove precipitated manganese dioxide, and the organic layer was separated and washed with water. The solvent was distilled leaving 2-hexyldecanoic acid (222 g) as a nearly colourless oil.

Workup

  1. filtrationThe mixture was filtered
  2. customto remove
  3. customprecipitated manganese dioxide
  4. customthe organic layer was separated
  5. washwashed with water
  6. distillationThe solvent was distilled

Sources & evidence

ORD record
ord-c21f48776e544bf9bd243286c815e764
Source dataset
uspto-grants-1993_10
Patent number
US05254695

Reaction notes

Loading…