p-Toluenesulfonic acid → 2-Cyclopentyl-3,5-xylenol

HRID 597105Notes

Reaction equation

HRID 597105 reaction equation
[CH:1]1[CH2:5][CH2:4][CH2:3][CH:2]=1.[CH3:6][C:7]1[CH:8]=[C:9]([OH:14])[CH:10]=[C:11]([CH3:13])[CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH3:6][C:7]1[C:8]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:9]([OH:14])[CH:10]=[C:11]([CH3:13])[CH:12]=1

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 79483,5-DimethylphenolHCID 8882Cyclopentene

Product 1

HCID 64540462-Cyclopentyl-3,5-xylenolYield 31.6%

Procedure

102 g of cyclopentene are added dropwise to 244 g of 3,5-dimethylphenol and 20 g of p-toluene sulphonic acid at 120° C. The mixture is then stirred at this temperature for 2 h. After removal of the catalyst by washing with sodium hydrogen carbonate solution the mixture is fractionated. At boiling point 104° C (0.5 mm Hg) 90 g of 3,5-dimethyl-2-cyclopentylphenol are obtained.

Workup

  1. customAfter removal of the catalyst
  2. washby washing with sodium hydrogen carbonate solution the mixture

Sources & evidence

ORD record
ord-f18cbb8fe8e4448890a27c7f95d2815c
Source dataset
uspto-grants-1977_03
Patent number
US04013473

Reaction notes

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