p-Toluenesulfonic acid → HCID 53832859, compound

HRID 1283576Notes

Reaction equation

HRID 1283576 reaction equation
[O:1]=[C:2]1[CH2:6][C:5]([CH3:8])([CH3:7])[CH:4]([CH:9]=[CH:10][C:11]([CH3:15])=[CH:12][CH:13]=[O:14])[CH:3]1[CH3:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1(C)C=CC=CC=1>[O:1]=[C:2]1[CH2:6][C:5]([CH3:7])([CH3:8])[C:4]([CH:9]=[CH:10][C:11]([CH3:15])=[CH:12][CH:13]=[O:14])=[C:3]1[CH3:16]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 54549039HCID 54549039, compound

Product 1

HCID 53832859HCID 53832859, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2 g. of the 5-(3-oxo-2,5,5-trimethyl-cyclopent-1-yl)-3-methyl-penta-2,4-dien-1-al, 50 mg. of p-toluenesulfonic acid, 2.5 g. of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and 40 ml. of toluene was heated to boiling for 5 hours under reflux conditions. After cooling, the mixture is filtered. After evaporation of the filtrate, there is obtained 5-(3-oxo-2,5,5-trimethyl-cyclopent-1-en-1-yl)-3-methyl-penta-2,4-dien-1-al which, after purification by adsorption on silica gel, has a melting point of 91°-93°C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. customAfter evaporation of the filtrate

Sources & evidence

ORD record
ord-247092e47459483b9fd3bdaa367e5f1f
Source dataset
uspto-grants-1976_08
Patent number
US03975445

Reaction notes

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