Sodium Bicarbonate → 2-Carboethoxy-2,4-dimethylcyclopent-4-en-5-olone

HRID 2296253Notes

Reaction equation

HRID 2296253 reaction equation
[C:1]([C:6]1([CH3:16])[CH2:10][CH:9]([CH3:11])[C:8](=[O:12])[C:7]1(C#N)[OH:13])([O:3][CH2:4][CH3:5])=[O:2].C([O-])(=O)C.[Na+].C(=O)([O-])O.[Na+]>O>[C:1]([C:6]1([CH3:16])[CH2:10][C:9]([CH3:11])=[C:8]([OH:12])[C:7]1=[O:13])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 204720793-Carboethoxy-2-cyano-2-hydroxy-3,5-dimethylcyclopentanone

Product 1

HCID 204720932-Carboethoxy-2,4-dimethylcyclopent-4-en-5-oloneYield 716.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

66.3 g (0.03 mol) of the foregoing 3-carboethoxy-2-cyano-2-hydroxy-3,5-dimethylcyclopentanone and 30.2 g (0.4 mol) of anhydrous sodium acetate are treated with 350 ml of water. The mixture is refluxed for 6 hours. For the working-up, the mixture is adjusted to pH 7 with saturated sodium hydrogen carbonate solution and then extracted four times with methylene chloride. The organic phases are dried over sodium sulphate, concentrated and dried in a high vacuum for 1 hour. (The product can, however, also be directly crystallised from the reaction mixture). There are obtained 42.6 g (73%) of crystalline 2-carboethoxy-2,4-dimethylcyclopent-4-en-5-olone of melting point 92°-93° C.

Workup

  1. temperatureThe mixture is refluxed for 6 hours
  2. extractionextracted four times with methylene chloride
  3. dry with materialThe organic phases are dried over sodium sulphate
  4. concentrationconcentrated
  5. customdried in a high vacuum for 1 hour
  6. custom(The product can, however, also be directly crystallised from the reaction mixture)

Sources & evidence

ORD record
ord-41b06f54a12b4729bb17d214cfb73421
Source dataset
uspto-grants-1984_01
Patent number
US04428886

Reaction notes

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