p-Toluenesulfonic acid → 4,8-Dimethylnona-3,7-dien-2-one

HRID 1580179Notes

Reaction equation

HRID 1580179 reaction equation
[CH3:1][C:2](OCC)([CH3:12])[CH2:3][C:4]([O:9]CC)(OCC)[CH3:5].[CH3:16][C:17]([CH3:21])=[CH:18][CH2:19]O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O-]CC.[Na+]>C(O)C>[CH3:12][C:2]([CH2:1][CH2:19][CH:18]=[C:17]([CH3:21])[CH3:16])=[CH:3][C:4](=[O:9])[CH3:5]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 111733-Methyl-2-buten-1-OLHCID 2723922Sodium ethoxideHCID 21565215HCID 21565215, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 100 parts of 4-methyl-2,2,4-triethoxypentane, 40 parts of prenol and 0.08 part of p-toluenesulfonic acid is heated for 6 hours at 140°C, the ethyl alcohol formed being distilled off continuously. On completion of the reaction, the reaction mixture is neutralized with sodium ethoxide and the reaction product is fractionally distilled. There are obtained 45.2 parts of 4,8-dimethyl-3,7-nonadien-2-one, equivalent to a yield of 86% and a conversion of 68% based on prenol.

Workup

  1. distillationbeing distilled off continuously
  2. customOn completion of the reaction
  3. distillationthe reaction product is fractionally distilled

Sources & evidence

ORD record
ord-590c99b752354972953087de2282b226
Source dataset
uspto-grants-1976_01
Patent number
US03932462

Reaction notes

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