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

HRID 2397291Notes

Reaction equation

HRID 2397291 reaction equation
[CH3:1][O-:2].[Na+].[CH3:4][CH:5]([CH2:7][CH2:8][CH2:9][CH:10]([CH2:12][CH:13]=[O:14])[CH3:11])[CH3:6]>CN(C)C=O>[CH3:11][C:10](/[CH:9]=[CH:8]/[CH2:7][CH:5]([CH3:4])[CH2:6][CH2:8][CH2:7][CH:5]([CH3:6])[CH3:4])=[CH:12][C:13]([O:2][CH3:1])=[O:14]

Participants

4

Reactant 2

HCID 1107473,7-DimethyloctanalHCID 10942334Sodium Methoxide

Product 1

HCID 131710730trans Methyl 3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium methoxide (1.2 g. of sodium and 30 ml. of methanol) is added slowly to a mixture of 5 g. of dihydrocitronellal and 10 g. of diethyl 3-methoxycarbonyl-2-methylprop-2-enyl phosphonate (about 77% trans) in 50 ml. of dimethylformamide, under nitrogen and at about 0°, with stirring. After addition is complete, the reaction is left three hours at room temperature and then worked up by extraction with hexane/ether to yield cis/trans methyl 3,7,11-trimethyldodeca-2,4-dienoate, mostly the trans,trans isomer.

Workup

  1. additionAfter addition
  2. extractionworked up by extraction with hexane/ether

Sources & evidence

ORD record
ord-98d4dbb3c3c540c29ae8c3e99cc0775b
Source dataset
uspto-grants-1977_05
Patent number
US04021461

Reaction notes

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