3-Carboethoxy-2-cyano-3,5-dimethylcyclopentanone → 3,5-Dimethylcyclopent-2-en-5-olone

HRID 2296256Notes

Reaction equation

HRID 2296256 reaction equation
[C:1]([C:6]1(C)[CH2:10][CH:9]([CH3:11])[C:8](=[O:12])[CH:7]1C#N)(OCC)=O.[OH:16]OS([O-])=O.[K+]>O>[CH3:1][C:6]1[CH2:10][C:9]([CH3:11])([OH:16])[C:8](=[O:12])[CH:7]=1

Participants

4

Reactant 2

HCID 125252633-Carboethoxy-2-cyano-3,5-dimethylcyclopentanoneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 204720903,5-Dimethylcyclopent-2-en-5-oloneYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The same product as that of paragraph (d) of Example 5 can also be obtained by treating 3-carboethoxy-2-cyano-3,5-dimethylcyclopentanone [see paragraph (a) of Example 5] with Caroat, acidifying the resulting mixture to pH 1 and then refluxing the mixture for 24 hours. Working-up as described in paragraph (d) of Example 5 yields 70% of pure crystalline 3,5-dimethylcyclopent-2-en-5-olone of melting point 92°-93° C. (from water).

Workup

  1. temperaturerefluxing the mixture for 24 hours

Sources & evidence

ORD record
ord-6eeef55880ac4828934e645b8bc41152
Source dataset
uspto-grants-1984_01
Patent number
US04428886

Reaction notes

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