Methanol → cis 3,7,11-Trimethyldodeca-2,4-dienoic acid

HRID 2397286Notes

Reaction equation

HRID 2397286 reaction equation
[CH3:1][C:2](/[CH:8]=[CH:9]\[CH2:10][CH:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:3][C:4]([O:6]C)=[O:5].CO.[OH-].[Na+]>O>[CH3:1][C:2](/[CH:8]=[CH:9]\[CH2:10][CH:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:3][C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86734712cis Methyl 3,7,11-trimethyldodeca-2,4-dienoate

Product 1

HCID 86734009cis 3,7,11-Trimethyldodeca-2,4-dienoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 1 g. of trans/cis methyl 3,7,11-trimethyldodeca-2,4-dienoate, 60 ml. of methanol, 0.5 g. of sodium hydroxide and 6 ml. of water is stirred at about 30° for about 56 hours. The mixture is then diluted with water, neutralized and extracted with ether. The organic phase is washed with water, dried over sodium sulfate and evaporated to yield trans/cis 3,7,11-trimethyldodeca-2,4-dienoic acid.

Workup

  1. additionA mixture of 1 g
  2. extractionextracted with ether
  3. washThe organic phase is washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-49a33885006c4aada526c0de44360c78
Source dataset
uspto-grants-1977_05
Patent number
US04021461

Reaction notes

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