Ethanol → 4,8,12-Trimethyltrideca-3,7,11-trienoic acid

HRID 2164330Notes

Reaction equation

HRID 2164330 reaction equation
C(C#N)[CH:2]=[C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])[CH3:9])[CH3:4].[OH-:18].[K+].[CH2:20]([OH:22])[CH3:21]>O>[CH3:4][C:3]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:2][CH2:21][C:20]([OH:18])=[O:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 1111274,8,12-Trimethyltrideca-3,7,11-trienenitrile

Product 1

HCID 537917614,8,12-Trimethyltrideca-3,7,11-trienoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 469 g (2.02 moles) farnesyl cyanide, 287 g potassium hydroxide, 2,500 ml ethanol and 340 ml water were heated under reflux. After 5 hours, the ethanol was evaporated and the residue poured into 10 liters of water. The aqueous solution so obtained was twice extracted with 1 liter diethyl ether, the extracts being discarded, and thereafter acidified with 20% sulfuric acid. Then, the free acid was extracted with diethyl ether. The etheric solution was again washed with water and dried with sodium sulfate. After evaporation of the ether, 419 g (83% of the theoretical) of homofarnesic acid were obtained as a yellow oil.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux
  3. customthe ethanol was evaporated
  4. additionthe residue poured into 10 liters of water
  5. customThe aqueous solution so obtained
  6. extractionwas twice extracted with 1 liter diethyl ether
  7. extractionThen, the free acid was extracted with diethyl ether
  8. washThe etheric solution was again washed with water
  9. dry with materialdried with sodium sulfate
  10. customAfter evaporation of the ether, 419 g (83% of the theoretical) of homofarnesic acid
  11. customwere obtained as a yellow oil

Sources & evidence

ORD record
ord-d220aeafb4da42cdaf67590c147bf58f
Source dataset
uspto-grants-1985_03
Patent number
US04503240

Reaction notes

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