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

HRID 1758108Notes

Reaction equation

HRID 1758108 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 hydrogen-carbonate solution, was dissolved 29 g of 4-hydroxy-4-methyl-5-allyl-2-cylcopentenone. 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-932137a7510447f9930e911bb98f95bc
Source dataset
uspto-grants-1983_02
Patent number
US04371711

Reaction notes

Loading…