Citronellol → 4-Oxo-decanoic Acid 3,7-dimethyl-oct-6-enyl Ester

HRID 1018160

Reaction equation

HRID 1018160 reaction equation
[O:1]=[C:2]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:14][C:15](=[CH:17][CH2:18][CH2:19][CH:20]([CH2:22][CH2:23]O)[CH3:21])[CH3:16]>C1CCCCC1.CCOCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:21][CH:20]([CH2:19][CH2:18][CH:17]=[C:15]([CH3:16])[CH3:14])[CH2:22][CH2:23][O:6][C:5](=[O:7])[CH2:4][CH2:3][C:2](=[O:1])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 2

HCID 8842CitronellolHCID 5386474-Oxo capric acid

Product 1

HCID 538305424-Oxo-decanoic Acid 3,7-dimethyl-oct-6-enyl EsterYield 91%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolventHCID 8078CyclohexaneSolvent

Procedure

A solution of 20.0 g 4-oxo-1-decanoic acid (Synthesis, 1987, 408), 16.8 g citronellol extra and 0.5 g p-toluene-sulfonic acid in 150 ml of cyclohexane was refluxed in a flask equipped with a Dean-Stark trap for 3 hours. Then the reaction mixture was cooled, diluted with ether, washed with saturated NaHCO3 and water. The organic phase was dried, filtered and evaporated to dryness. The resulting oil was purified by chromatography to yield 31.7 g of a yellow oil.

Workup

  1. customequipped with a Dean-Stark trap for 3 hours
  2. temperatureThen the reaction mixture was cooled
  3. washwashed with saturated NaHCO3 and water
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting oil was purified by chromatography

Sources & evidence

ORD record
ord-11630feaa8de4c1b838b6cbecb81d087
Source dataset
uspto-grants-2002_11
Patent number
US06479682B1

Linked notes

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