3,7-Dimethyl-7-ethoxyoctanal → Ethyl 11-ethoxy-3,7,11-trimethyldodeca-2,4-dienoate

HRID 918316Notes

Reaction equation

HRID 918316 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[CH2:5]([O:7][C:8]([CH3:18])([CH3:17])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:16])[CH2:13][CH:14]=O)[CH3:6]>CN(C)C=O>[CH2:5]([O:7][C:8]([CH3:18])([CH3:17])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:16])[CH2:13][CH:14]=[CH:9][C:8]([CH3:17])=[CH:3][C:2]([O:7][CH2:5][CH3:6])=[O:1])[CH3:6]

Participants

4

Reactant 2

HCID 1607073,7-Dimethyl-7-ethoxyoctanalHCID 2723922Sodium ethoxide

Product 1

HCID 53878158Ethyl 11-ethoxy-3,7,11-trimethyldodeca-2,4-dienoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium ethoxide (prepared from 0.2 g. of sodium and 12 ml. of ethanol) is slowly added to a mixture of 1.1 g. of 7-ethoxy-3,7-dimethyloctan-1-al, diethyl 3-ethoxycarbonyl-2-methylprop-2-enyl phosphonate and 50 ml. of dimethylformamide, with stirring, under nitrogen, at 0°. The reaction is stirred for 1.5 hours after addition is complete and then worked up by extraction with ether to yield ethyl 11-ethoxy-3,7,11-trimethyldodeca-2,4-dienoate, mostly trans(2), trans(4), which can be further purified by chromatography and distillation.

Workup

  1. additionafter addition
  2. extractionworked up by extraction with ether

Sources & evidence

ORD record
ord-7e41b92396334c159995518d12681bca
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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