Water → Cyclopentanone, 2-(2-oxo-2-phenylethyl)-

HRID 1973466Notes

Reaction equation

HRID 1973466 reaction equation
[CH2:1](Br)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=CC=1.N1(C2CCCC=2)CCCC1.[OH2:28]>>[CH2:1]([CH:17]1[CH2:14][CH2:15][CH2:16][C:11]1=[O:28])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 6259Phenacyl bromideHCID 81570Pyrrolidine, 1-(1-cyclopenten-1-yl)-

Product 1

HCID 10655725Cyclopentanone, 2-(2-oxo-2-phenylethyl)-

Procedure

A solution of 72.4 g (0.36 mole) of phenacyl bromide in 175 ml. of toluene is added dropwise to a stirred boiling solution of 50 g (0.036 mole) of 1-pyrrolidino-1-cyclopentene and 200 ml. of toluene. The reaction mixture is heated under reflux for 3 hours. diluted cautiously with 200 ml. of water, refluxed for 4 hours and cooled. After the layers separate, the aqueous phase is extracted with benzene, and the organic phase is dried and concentrated to an oil. Distillation gives 2-phenacylcyclopentanone as a liquid, b.p. 138°-140° C. (0.05 mm).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 3 hours
  3. additiondiluted cautiously with 200 ml
  4. temperaturecooled
  5. customAfter the layers separate
  6. extractionthe aqueous phase is extracted with benzene
  7. customthe organic phase is dried
  8. concentrationconcentrated to an oil
  9. distillationDistillation

Sources & evidence

ORD record
ord-e7e497e72e1e43f4901b79032a6ba84d
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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