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

HRID 1658631Notes

Reaction equation

HRID 1658631 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.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>O>[CH3:7][C:8](=[CH:9][CH2:10][CH2:1][C:2](=[CH:3][CH:4]=[O:5])[CH3:6])[CH3:12]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 111733-Methyl-2-buten-1-OLHCID 610203-Methyl-2-butenal

Product 1

HCID 88433,7-Dimethylocta-2,6-Dienal

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 parts of 3-methyl-2-buten-1-ol is brought to refluxing temperature (140°C) and 100 parts of 3,3-dimethylacrolein in which 2 parts of dibenzoyl peroxide has been dissolved is introduced in the course of one hour while stirring. The reaction mixture is then heated for another three hours at 140°C, while the water formed is continuously removed using pentane as entrainer. Working up gives 105 parts of citral. The yield is thus 86% of theory based on 3,3-dimethylacrolein at a conversion of 67%.

Workup

  1. dissolutionhas been dissolved
  2. additionis introduced in the course of one hour
  3. customformed
  4. customis continuously removed

Sources & evidence

ORD record
ord-943529e92c8e462daa08c27f5855364c
Source dataset
uspto-grants-1976_06
Patent number
US03965193

Reaction notes

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