p-Toluenesulfonic acid → 1-(2,2-Dimethyl-6-methylenecyclohexyl)-2-buten-1-one

HRID 1579754Notes

Reaction equation

HRID 1579754 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[C:10](=[O:15])[CH2:11][CH:12](N)[CH3:13].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Na]>C1(C)C=CC=CC=1.O>[CH2:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[CH:3]1[C:10](=[O:15])[CH:11]=[CH:12][CH3:13]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 5360545SodiumHCID 21569478HCID 21569478, compound

Product 1

HCID 566317481-(2,2-Dimethyl-6-methylenecyclohexyl)-2-buten-1-oneYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

1 g of 2-methylene-6,6-dimethyl-1-[3-amino-butanoyl]-cyclohexane in 25 ml of toluene was refluxed for 3 hours in the presence of a catalytic amount of p-toluene-sulphonic acid. The obtained solution was wahsed with a 10% solution of sodium hydrogenocarbonate in water until neutrality, then dried and concentrated. 0.6 g of 2-methylene-6,6-dimethyl-1-[but-2-enoyl]-cyclohexane was thus obtained. The analytical data were in agreement with those of a pure sample prepared by one of the known methods.

Workup

  1. customdried
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5e07e788c6d248c9b94ef43465e53c7e
Source dataset
uspto-grants-1976_01
Patent number
US03931323

Reaction notes

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