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

HRID 1579873Notes

Reaction equation

HRID 1579873 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 was added dropwise during 30 minutes to a stirred, boiling solution of 50.0 g. (0.36 mole) of 1-pyrrolidino-1-cyclopentene and 200 ml. of toluene. The mixture was heated under reflux for 3 hours, diluted cautiously with 200 ml. of water, refluxed for 4 hours and cooled. The layers were separated, the aqueous phase extracted with benzene, and the combined organic phase was dried over sodium sulfate and concentrated to an oil. Distillation gave 24.8 g. (34%) of liquid, b.p. 138°-140° (0.05 mm.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. additiondiluted cautiously with 200 ml
  4. temperaturecooled
  5. customThe layers were separated
  6. extractionthe aqueous phase extracted with benzene
  7. dry with materialthe combined organic phase was dried over sodium sulfate
  8. concentrationconcentrated to an oil
  9. distillationDistillation
  10. customgave 24.8 g

Sources & evidence

ORD record
ord-a4c63a3325544291908a793eadecd2f3
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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