Ethanol → 3,7,11-Trimethyldodeca-2,4-dienoic acid

HRID 1576589Notes

Reaction equation

HRID 1576589 reaction equation
C(O)C.[OH-].[Na+].[CH3:6][C:7]([CH:14]=[CH:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:8][C:9]([O:11]CC)=[O:10]>O>[CH3:6][C:7]([CH:14]=[CH:15][CH2:16][CH:17]([CH3:24])[CH2:18][CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[CH:8][C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 38759Ethyl 3,7,11-trimethyldodeca-2,4-dienoate

Product 1

HCID 1037233,7,11-Trimethyldodeca-2,4-dienoic acidYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 350 ml. of ethanol, 105 ml. of water and 70 ml. of 50% aqueous sodium hydroxide is added 46.5 g. of ethyl 3,7,11-trimethyldodeca-2,4-dienoate (40% cis, trans and 60% trans, trans). The mixture is refluxed for about 19 hours. After cooling, ethanol is removed under reduced pressure and water added followed by extraction with ether to yield 3,7,11-trimethyldodeca-2,4-dienoic acid containing about 58% trans, trans isomer. Conversion of the thus-obtained acid to the S-benzyl-isothiouronium salt recrystallized from aqueous methanol, and regeneration of the acid with ether-aqueous hydrochloric acid provides crystalline trans, trans, 3,7,11-trimethyldodeca-2,4-dienoic acid.

Workup

  1. temperatureThe mixture is refluxed for about 19 hours
  2. temperatureAfter cooling
  3. customethanol is removed under reduced pressure and water
  4. additionadded
  5. extractionfollowed by extraction with ether

Sources & evidence

ORD record
ord-4cc709b6430f44c5affb161ef85850a1
Source dataset
uspto-grants-1976_09
Patent number
US03981922

Reaction notes

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