Mesityl oxide → 4,8-Dimethylnona-3,7-dien-2-one

HRID 1076000Notes

Reaction equation

HRID 1076000 reaction equation
[O:1]=[C:2]([CH:4]=[C:5]([CH3:7])[CH3:6])[CH3:3].[CH3:8][C:9]([CH3:13])=[CH:10][CH2:11]O>C(O)=O>[CH3:6][C:5]([CH2:7][CH2:11][CH:10]=[C:9]([CH3:13])[CH3:8])=[CH:4][C:2](=[O:1])[CH3:3]

Participants

4

Reactant 2

HCID 8858Mesityl oxideHCID 111733-Methyl-2-buten-1-OL

Product 1

HCID 5496634,8-Dimethylnona-3,7-dien-2-oneYield 78%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

800 parts of mesityl oxide, 200 parts of 3-methyl-2-buten-1-ol (prenol) and 2 parts of formic acid are heated at 250°C for 3 hours in a vibrated autoclave holding 2500 parts by volume at a pressure of 60 atmospheres. The reaction mixture is worked up by distillation and gives 190 parts of 4,8-dimethyl-3,7-nonadien-2-one having a boiling point of 60° to 62°C at 0.2 mm. The yield is 78% of theory at a conversion of 63% based on prenol.

Workup

  1. distillationThe reaction mixture is worked up by distillation

Sources & evidence

ORD record
ord-b28cc8d15f99425bae1cf3e653404651
Source dataset
uspto-grants-1976_05
Patent number
US03954804

Reaction notes

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