Water → 4-Hydroxy-4-methyl-5-propylcyclopent-2-en-1-one

HRID 1073694Notes

Reaction equation

HRID 1073694 reaction equation
[CH3:1][C:2]1[O:11][C:5]([CH:6](O)[CH2:7][CH2:8][CH3:9])=[CH:4][CH:3]=1.[OH2:12]>>[CH2:7]([CH:6]1[C:2]([OH:11])([CH3:1])[CH:3]=[CH:4][C:5]1=[O:12])[CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 962WaterHCID 15702043HCID 15702043, compound

Product 1

HCID 130367894-Hydroxy-4-methyl-5-propylcyclopent-2-en-1-oneYield 81%

Procedure

Into a four necked flask equipped with an agitator and a thermometer, 5-methyl-α-n-propyl-furfuryl alcohol (40 parts) and water (1200 parts) were charged, and the resultant mixture was stirred at a temperature of 95° to 100° C. in a nitrogen stream, during which the pH was maintained at 4.9 to 5.3. After confirming the complete consumption of the starting compound by gas chromatography, the reaction mixture was cooled and extracted with methyl isobutyl ketone. The extract was concentrated to give 2-n-propyl-3-hydroxy-3-methyl-4-cyclopentenone in a yield of 81 %.

Workup

  1. customInto a four necked flask equipped with an agitator
  2. temperaturewas maintained at 4.9 to 5.3
  3. customthe complete consumption of the starting compound by gas chromatography
  4. temperaturethe reaction mixture was cooled
  5. extractionextracted with methyl isobutyl ketone
  6. concentrationThe extract was concentrated

Sources & evidence

ORD record
ord-71db375e4f8a450eba54e35b3ee8f3ee
Source dataset
uspto-grants-1990_11
Patent number
US04970345

Reaction notes

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