Potassium Hydroxide → HCID 11788723, compound

HRID 1108765Notes

Reaction equation

HRID 1108765 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH:11]([CH2:17][C:18](=O)C)C(OCC)=O)=[CH:5][CH:4]=1.[OH-:22].[K+]>O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:10][CH2:11][C:17](=[O:22])[CH:18]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium Hydroxide4×HCID 18784184HCID 18784184, compound

Product 1

HCID 11788723HCID 11788723, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethyl 2-[2-(4-methoxyphenyl)-2-oxoethyl]-4-oxopentanoate (26.2 g) there was added 1000 ml of 1% aqueous potassium hydroxide solution, and the mixture was refluxed for an hour. Next, potassium hydroxide was added so that the aqueous potassium hydroxide solution reached a concentration of 10% (adding a solution of 146 g of potassium hydroxide in 200 ml of water), and the mixture was further refluxed for 2 hours. After allowing the reaction solution to cool, extraction was performed with ethyl acetate and water washing was then followed by drying with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to produce crude crystals which were then washed with diethyl ether to give 11.4 g of 3-(4-methoxyphenyl)-2-cyclopenten-1-one (64.4% yield).

Workup

  1. temperaturethe mixture was refluxed for an hour
  2. temperaturewas further refluxed for 2 hours
  3. temperatureto cool
  4. extractionextraction
  5. dry with materialby drying with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto produce crude crystals which
  8. washwere then washed with diethyl ether

Sources & evidence

ORD record
ord-bf6c14709da7489a87b1727d927acd7e
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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