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

HRID 68019

Reaction equation

HRID 68019 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.[Cl-].[Na+].[OH2:14]>>[CH2:7]([C:6]1[C:5](=[O:10])[CH2:4][CH:3]([OH:14])[C:2]=1[CH3:11])[CH:8]=[CH2:9]

Participants

4

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 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)-

Procedure

In an autoclave, 4-hydroxy-4-methyl-5-allyl-2-cyclopentenone (20 g) and water (400 ml) were charged, and the resultant mixture was stirred at 180° C. for 6 hours in a nitrogen atmosphere. After cooling, sodium chloride (50 g) was added to the reaction mixture, and the resulting mixture was extracted with methyl isobutyl ketone. The extract was concentrated under reduced pressure to give 2-allyl-3-methyl-4-hydroxy-2-cyclopentenone (19 g). Yield, 95%. M.P. 130°-132° C./1.2 mmHg.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting mixture was extracted with methyl isobutyl ketone
  3. concentrationThe extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8371605ffe1349dc8bb6c0fe1adc2020
Source dataset
uspto-grants-1982_08
Patent number
US04347386

Linked notes

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