CID 406 → Ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate

HRID 918307Notes

Reaction equation

HRID 918307 reaction equation
[CH3:1][CH:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:11])[CH3:10])[CH2:3][CH:4]=[O:5].P(=O)([O-])[O-].[H][H].[O-:18][CH2:19][CH3:20].[Na+]>CCOCC.CN(C)C=O>[CH3:1][C:2]([CH:6]=[CH:7][CH2:8][CH:9]([CH3:10])[CH2:11][CH2:4][CH:3]=[C:2]([CH3:6])[CH3:1])=[CH:3][C:4]([O:18][CH2:19][CH3:20])=[O:5]

Participants

7

Reactant 4

HCID 406CID 406HCID 7794CitronellalHCID 2723922Sodium ethoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 54528342Ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of one g. of 3,7-dimethyloct-6-en-1-al 1.5 g. of phosphonate (II; R' is ethyl, R1 is methyl, R6 is ethoxy, R12 is hydrogen) and 50 ml. of dimethylformamide, under nitrogen, is slowly added sodium ethoxide (prepared from 200 mg. of sodium and 12 ml. of ethanol). The mixture is allowed to stand at room temperature for one hour and then is worked up with ether. The ethereal extracts are dried, concentrated and then chromatographed on silica plates eluting with hexane/ether to yield ethyl 3,7,11-trimethyldodeca-2,4,10-trienoate which is predominantly trans at position C-2,3 and C-4,5.

Workup

  1. additionTo a mixture of one g
  2. customThe ethereal extracts are dried
  3. concentrationconcentrated
  4. customchromatographed on silica plates
  5. washeluting with hexane/ether

Sources & evidence

ORD record
ord-a38a8b2bd3f34ebc892789ca59bbfd23
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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