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

HRID 2304948Notes

Reaction equation

HRID 2304948 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-ed37327287c64f4598cad3fa78b6dcdb
Source dataset
uspto-grants-2002_08
Patent number
US06437150B1

Reaction notes

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