Sodium Bicarbonate → 2-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-

HRID 358295

Reaction equation

HRID 358295 reaction equation
O[C:2]1([CH3:11])[CH:6]([CH2:7][CH:8]=[CH2:9])[C:5](=[O:10])[CH:4]=[CH:3]1.C(=O)([O-])[OH:13].[Na+]>>[CH2:7]([C:6]1[C:5](=[O:10])[CH2:4][CH:3]([OH:13])[C:2]=1[CH3:11])[CH:8]=[CH2:9]

Participants

3

Reactant 2

HCID 516892Sodium BicarbonateHCID 128798724-Hydroxy-4-methyl-5-(prop-2-en-1-yl)cyclopent-2-en-1-one

Product 1

HCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-Yield 75%

Procedure

In 200 ml of a 5% aqueous sodium hydrogencarbonate solution, was dissolved 29 g of 4-hydroxy-4-methyl-5-allyl-2-cyclopentenone. The solution was heated with stirring under reflux for one hour. After having been allowed to cool, the reaction mixture was extracted three times with chloroform. The extract solution was dried over anhydrous magnesium sulfate and freed from the chloroform by distillation. The residue was distilled in vacuo to obtain 21.7 g (75% yield) of 2-allyl-3-methyl-4-hydroxy-2-cyclopentenone boiling at 155° C./1 mmHg.

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for one hour
  3. temperatureto cool
  4. extractionthe reaction mixture was extracted three times with chloroform
  5. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  6. distillationfreed from the chloroform by distillation
  7. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-cd46fe39913045f795d3913d5218cf2d
Source dataset
uspto-grants-1984_08
Patent number
US04465862

Linked notes

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