Ethanol → 11-Methylthio-3,7,11-trimethyldodeca-2,4-dienoic acid

HRID 1605134Notes

Reaction equation

HRID 1605134 reaction equation
C(O)C.[OH-].[Na+].[CH3:6][S:7][C:8]([CH3:25])([CH3:24])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:23])[CH2:13][CH:14]=[CH:15][C:16]([CH3:22])=[CH:17][C:18]([O:20]C)=[O:19]>O>[CH3:6][S:7][C:8]([CH3:24])([CH3:25])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:23])[CH2:13][CH:14]=[CH:15][C:16]([CH3:22])=[CH:17][C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 53938725Methyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate

Product 1

HCID 5422430711-Methylthio-3,7,11-trimethyldodeca-2,4-dienoic acid

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 methyl 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoate. The mixture is refluxed for about 18 hours. After cooling, alcohol is removed in vacuo. Water is added followed by acidification and then extraction with ether to yield 11-methylthio-3,7,11-trimethyldodeca-2,4-dienoic acid.

Workup

  1. temperatureThe mixture is refluxed for about 18 hours
  2. temperatureAfter cooling
  3. customalcohol is removed in vacuo
  4. additionWater is added
  5. extractionextraction with ether

Sources & evidence

ORD record
ord-4761d3fbe20644ffa11e52030102de9b
Source dataset
uspto-grants-1976_04
Patent number
US03948996

Reaction notes

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