Sulfuric Acid → 2-Hexyldecanoic acid

HRID 1638390Notes

Reaction equation

HRID 1638390 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 precipitate 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 precipitate manganese dioxide
  3. customthe organic layer was separated
  4. washwashed with water
  5. distillationThe solvent was distilled

Sources & evidence

ORD record
ord-5a6c9838b94a468aa56b8e9a2ace6115
Source dataset
uspto-grants-1989_11
Patent number
US04879388

Reaction notes

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