3,7-Dimethyl-7-ethoxyoctanal → 10-Ethoxy-6,10-dimethylundec-3-en-2-one

HRID 918321Notes

Reaction equation

HRID 918321 reaction equation
[CH2:1]([O:3][C:4]([CH3:14])([CH3:13])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:12])[CH2:9][CH:10]=O)[CH3:2]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH3:14])([CH3:13])[CH2:5][CH2:6][CH2:7][CH:8]([CH3:12])[CH2:9][CH:10]=[CH:5][C:4](=[O:3])[CH3:13])[CH3:2]

Participants

3

Reactant 1

HCID 1607073,7-Dimethyl-7-ethoxyoctanal

Product 1

HCID 5375466210-Ethoxy-6,10-dimethylundec-3-en-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 9.0 g. of 7-ethoxy-3,7-dimethyloctan-1-al and 15 g. of triphenylphosphineacetylmethylene in 100 ml. of dry toluene, under nitrogen, is refluxed for 20 hours. Thereafter, the toluene is evaporated and pentane added to remove triphenylphosphine. After concentration, the product is distilled to yield 10-ethoxy-6,10dimethylundec-3-en-2-one. The thus-prepared ketone is reacted with the carbanion of diethyl carbethoxymethylphosphonate using the procedure of Example 1 or 9 to prepare ethyl-11-ethoxy-3,7,11-trimethyldodeca-2,4-dienoate.

Workup

  1. additionA mixture of 9.0 g
  2. customThereafter, the toluene is evaporated
  3. additionpentane added
  4. customto remove triphenylphosphine
  5. concentrationAfter concentration
  6. distillationthe product is distilled

Sources & evidence

ORD record
ord-35c361016a5843989ffed8555fc53711
Source dataset
uspto-grants-1976_07
Patent number
US03970704

Reaction notes

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