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

HRID 2397290Notes

Reaction equation

HRID 2397290 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[CH3:5][CH:6]([CH2:8][CH2:9][CH2:10][CH:11]([CH2:13][CH:14]=[O:15])[CH3:12])[CH3:7]>CN(C)C=O>[CH3:12][C:11]([CH:10]=[CH:9][CH2:8][CH:6]([CH3:5])[CH2:7][CH2:9][CH2:8][CH:6]([CH3:7])[CH3:5])=[CH:13][C:14]([O:1][CH2:2][CH3:3])=[O:15]

Participants

4

Reactant 2

HCID 1107473,7-DimethyloctanalHCID 2723922Sodium ethoxide

Product 1

HCID 38759Ethyl 3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium ethoxide (9 g. sodium in 600 ml. of ethanol) is added slowly to a mixture of 42 g. of dihydrocitronellal and 75 g. of diethyl 3-ethoxycarbonyl-2-methylprop-2-enyl phosphonate (about 49% trans) in one liter of dimethylformamide, under nitrogen and at 0°, with stirring. The mixture is allowed to stand overnight at about 5° and the reaction worked up by extraction with ether, washing with water and brine and filtering through Florisil to yield ethyl 3,7,11-trimethyldodeca-2,4-dienoate as a cis/trans mixture, mostly trans,trans.

Workup

  1. extractionthe reaction worked up by extraction with ether
  2. washwashing with water and brine
  3. filtrationfiltering through Florisil

Sources & evidence

ORD record
ord-13765b556f8d49c181ab2df123e2e4c6
Source dataset
uspto-grants-1977_05
Patent number
US04021461

Reaction notes

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