Water → 2-Hexyl-2-cyclopenten-1-one

HRID 1073697Notes

Reaction equation

HRID 1073697 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4](S(O)(=O)=O)=[CH:3][CH:2]=1.[C:12]1(C)C=C[CH:15]=[CH:14][CH:13]=1.[OH2:19]>>[CH2:1]([C:6]1[C:5](=[O:19])[CH2:4][CH2:3][CH:2]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 962WaterHCID 1140TolueneHCID 6101p-Toluenesulfonic acid

Product 1

HCID 667682-Hexyl-2-cyclopenten-1-oneYield 97%

Procedure

The above prepared mixture (25 parts) was admixed with p-toluenesulfonic acid (1.25 parts) and toluene (75 parts) and refluxed for 2 hours, during which by-produced water was eliminated by azeotropic distillation. The reaction mixture was treated as in Example 1 to give 2-n-hexyl-2-cyclopentenone in a yield of 97 %.

Workup

  1. customThe above prepared mixture (25 parts)
  2. temperaturerefluxed for 2 hours, during which
  3. distillationwas eliminated by azeotropic distillation
  4. additionThe reaction mixture was treated as in Example 1

Sources & evidence

ORD record
ord-f0a1d5ac81a641f29422c21b54eac18b
Source dataset
uspto-grants-1990_11
Patent number
US04970345

Reaction notes

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