Water → 4-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one

HRID 68020

Reaction equation

HRID 68020 reaction equation
O[C:2]1([CH3:11])[CH:6]([CH2:7][C:8]#[CH:9])[C:5](=[O:10])[CH:4]=[CH:3]1.[Cl-].[Na+].[OH2:14]>>[CH2:7]([C:6]1[C:5](=[O:10])[CH2:4][CH:3]([OH:14])[C:2]=1[CH3:11])[C:8]#[CH:9]

Participants

4

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 130367862-Propargyl-3-hydroxy-3-methyl-4-cyclopentenone

Product 1

HCID 129182064-Hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentene-1-one

Procedure

In an autoclave, 4-hydroxy-4-methyl-5-propargyl-2-cyclopentenone (3 g) and water (400 ml) were charged, and the resultant mixture was stirred at 150° C. for 6 hours in a nitrogen atmosphere. After cooling, sodium chloride (50 g) was added to the reaction mixture, the resulting mixture was extracted with ethyl acetate. The extract was concentrated under reduced pressure and purified on column chromatography to give 2-propargyl-3-methyl-4-hydroxy-2-cyclopentenone (2.7 g). Yield, 90% nD21 1.5148.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. concentrationThe extract was concentrated under reduced pressure
  4. custompurified on column chromatography

Sources & evidence

ORD record
ord-2b26c2e712b8490caf387987e32d66da
Source dataset
uspto-grants-1982_08
Patent number
US04347386

Linked notes

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