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

HRID 365171Notes

Reaction equation

HRID 365171 reaction equation
C(O[C:5]1([CH3:14])[CH:9]=[CH:8][C:7](=[O:10])[CH:6]1[CH2:11][CH:12]=[CH2:13])(=O)C.[OH2:15]>C(O)(=O)C>[CH2:11]([C:6]1[C:7](=[O:10])[CH2:8][CH:9]([OH:15])[C:5]=1[CH3:14])[CH:12]=[CH2:13]

Participants

4

Reactant 2

HCID 962WaterHCID 13335393HCID 13335393, compound

Product 1

HCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-Yield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In the same flask as in Example 1, there were charged 3-acetoxy-2-allyl-3-methyl-4-cyclopentenone (3.0 g), water (10 g) and acetic acid (5 g), and the resultant mixture was stirred under reflux for 10 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and extracted three times with methyl isobutyl ketone (60 ml). The organic layers were combined together, washed with water and dried over magnesium sulfate. After concentration under reduced pressure, the residue was purified by column chromatography to give 1.95 g of 2-allyl-4-hydroxy-3-methyl-2-cyclopentenone. Yield, 83%.

Workup

  1. temperatureunder reflux for 10 hours
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. extractionextracted three times with methyl isobutyl ketone (60 ml)
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c0a3c93f68014ee287ff1d653ba17c30
Source dataset
uspto-grants-1986_08
Patent number
US04608442

Reaction notes

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