Hydrogen Peroxide → 3,7-Dimethylocta-2,6-Dienal

HRID 1658632Notes

Reaction equation

HRID 1658632 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][OH:5].[CH3:7][C:8]([CH3:12])=[CH:9][CH:10]=O.COCCO.OO>O>[CH3:7][C:8](=[CH:9][CH2:10][CH2:1][C:2](=[CH:3][CH:4]=[O:5])[CH3:6])[CH3:12]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 80192-MethoxyethanolHCID 111733-Methyl-2-buten-1-OLHCID 610203-Methyl-2-butenal

Product 1

HCID 88433,7-Dimethylocta-2,6-DienalYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100 parts of 3-methyl-2-buten-1-ol, 100 parts of 3,3-dimethylacrolein, 200 parts of ethylene glycol monomethyl ether and 3 parts of 30% aqueous hydrogen peroxide solution is heated under reflux for six hours while stirring and the water formed is removed continuously using pentane as entrainer. Fractional distillation of the reaction product gives 84.5 parts of citral, equivalent to a yield of 88% of theory, at a conversion of 53% (based on 3,3-dimethylacrolein).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for six hours
  3. customis removed continuously using pentane as entrainer
  4. distillationFractional distillation of the reaction product

Sources & evidence

ORD record
ord-61f2324366dc41ccbb994942a1a9e87f
Source dataset
uspto-grants-1976_06
Patent number
US03965193

Reaction notes

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