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

HRID 1076001Notes

Reaction equation

HRID 1076001 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.CC(C)=CC(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 3

HCID 8858Mesityl oxideHCID 109313-Methyl-2-butenoic acidHCID 111733-Methyl-2-buten-1-OL

Product 1

HCID 5496634,8-Dimethylnona-3,7-dien-2-oneYield 86%

Procedure

A mixture of 400 parts of mesityl oxide, 100 parts of prenol and 5 parts of 3,3-dimethylacrylic acid is heated for 4 hours at a pressure of 1.9 atmospheres and a temperature of 175°C in a still provided with means for removing water. The water formed is removed azeotropically. The reaction mixture is worked up. 85 parts of 4,8-dimethyl-3,7-nonadien-2-one is obtained. This is equivalent to a yield of 86% of theory at a conversion of 51% based on prenol.

Workup

  1. temperatureis heated for 4 hours at a pressure of 1.9 atmospheres
  2. customa temperature of 175°C in a still provided with means
  3. customfor removing water
  4. customThe water formed
  5. customis removed azeotropically

Sources & evidence

ORD record
ord-0eeaa70032bb4dd48a4d2a610f77f090
Source dataset
uspto-grants-1976_05
Patent number
US03954804

Reaction notes

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