Potassium Hydroxide → 2-Cyclopenten-1-one, 4,4-diphenyl-

HRID 1657274Notes

Reaction equation

HRID 1657274 reaction equation
[C:1]([CH2:4][C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:6]=O)(=[O:3])[CH3:2].[OH-].[K+]>O1CCCC1.CO>[C:8]1([C:5]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:4][C:1](=[O:3])[CH:2]=[CH:6]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 105627693-Acetyl-2,2-diphenylpropionaldehyde

Product 1

HCID 108898542-Cyclopenten-1-one, 4,4-diphenyl-Yield 87.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-acetyl-2,2-diphenylpropionaldehyde (48.9 g) in a mixture of tetrahydrofuran (55 ml) and methanol (30 ml) was added 10% aqueous solution of potassium hydroxide (15 ml) at room temperature. The solution was stirred for 2 hours and evaporated in vacuo. To the residue was added brine and extracted with diethyl ether. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (5:1) as an eluent to give 4,4-diphenyl-2-cyclopenten-1-one (39.76 g).

Workup

  1. customevaporated in vacuo
  2. additionTo the residue was added brine
  3. extractionextracted with diethyl ether
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and ethyl acetate (5:1) as an eluent

Sources & evidence

ORD record
ord-f56f2faca2214d5ab27a34aca91a28e7
Source dataset
uspto-grants-1993_10
Patent number
US05256824

Reaction notes

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