p-Toluenesulfonic acid → Piperitenone

HRID 1657965Notes

Reaction equation

HRID 1657965 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH:4]=[O:5].[C:7]1([CH3:17])[CH:12]=CC(S(O)(=O)=O)=[CH:9][CH:8]=1>O1CCCC1>[CH3:1][C:2]1[CH2:6][CH2:9][C:8](=[C:7]([CH3:17])[CH3:12])[C:4](=[O:5])[CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 610203-Methyl-2-butenal

Product 1

HCID 381152PiperitenoneYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 200 parts of 3,3-dimethylacrolein and 600 parts of tetrahydrofuran is heated with 0.008 part of p-toluenesulfonic acid in an autoclave for three hours at a pressure of 50 atmospheres and a temperature of 210°C. The reaction product is worked up by distillation. 72.5 parts of piperitenone is obtained. The yield is 78% of theory at a conversion of 52%.

Workup

  1. customa temperature of 210°C
  2. distillationThe reaction product is worked up by distillation

Sources & evidence

ORD record
ord-0091130655ca4e1b8bffdf527e650b81
Source dataset
uspto-grants-1976_06
Patent number
US03962341

Reaction notes

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