Propionic Acid → (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienal

HRID 1658633Notes

Reaction equation

HRID 1658633 reaction equation
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6]/[C:7](=[CH:9]/[CH2:10][OH:11])/[CH3:8])[CH3:3].[CH3:12][C:13]([CH3:17])=[CH:14][CH:15]=O.C(O)(=O)CC>>[CH3:12][C:13]([CH3:17])=[CH:14][CH2:15][CH2:3]/[C:2](/[CH3:1])=[CH:4]/[CH2:5][CH2:6]/[C:7](/[CH3:8])=[CH:9]/[CH:10]=[O:11]

Participants

4

Reactant 3

HCID 1032Propionic AcidHCID 610203-Methyl-2-butenalHCID 637566Geraniol

Product 1

HCID 5280598(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienalYield 84%

Procedure

100 parts of geraniol, 30 parts of 3,3-dimethylacrolein and 2.5 parts of propionic acid are heated together at refluxing temperature for four hours while stirring. The product is distilled. 83.5 parts of farnesal is obtained having a boiling point of 120° to 123°C at 0.2 mm. The yield is 84% of theory at a conversion of 63% (based on 3,3-dimethylacrolein).

Workup

  1. temperatureat refluxing temperature for four hours
  2. distillationThe product is distilled

Sources & evidence

ORD record
ord-54e530e68f6b4a7381ad12cf54aa1d36
Source dataset
uspto-grants-1976_06
Patent number
US03965193

Reaction notes

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