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

HRID 2397196Notes

Reaction equation

HRID 2397196 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-dcc78a1236ac4b0f8b26e0fa0fda19e8
Source dataset
uspto-grants-1977_05
Patent number
US04021411

Reaction notes

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