3,7-Dimethyloctanal → Methyl 3,7,11-trimethyldodeca-2,4-dienoate

HRID 2397292Notes

Reaction equation

HRID 2397292 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][CH:7]([CH2:9][CH:10]=[O:11])[CH3:8])[CH3:3].[CH3:12][O-:13].[Na+]>CN(C)C=O>[CH3:8][C:7]([CH:6]=[CH:5][CH2:4][CH:2]([CH3:1])[CH2:3][CH2:5][CH2:4][CH:2]([CH3:3])[CH3:1])=[CH:9][C:10]([O:13][CH3:12])=[O:11]

Participants

4

Reactant 2

HCID 1107473,7-DimethyloctanalHCID 10942334Sodium Methoxide

Product 1

HCID 54376380Methyl 3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.5 g. of dihydrocitronellal, 2.7 g. of diethyl 3-ethoxycarbonyl-2-methylprop-2-enyl phosphonate and 5 ml. of dimethylformamide, under nitrogen and at 0°, with stirring, is added slowly sodium methoxide (250 mg. sodium and 5 ml. of methanol). After addition is complete, the reaction is left two hours at room temperature and then worked up by extraction with ether/hexane to yield methyl 3,7,11-trimethyldodeca-2,4-dienoate.

Workup

  1. additionTo a mixture of 1.5 g
  2. additionAfter addition
  3. extractionworked up by extraction with ether/hexane

Sources & evidence

ORD record
ord-176681852b8342fe8d1ae8b10b7dd3a7
Source dataset
uspto-grants-1977_05
Patent number
US04021461

Reaction notes

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