Water → 2-(2-Oxo-2-phenylethyl)cyclohexanone

HRID 1579856Notes

Reaction equation

HRID 1579856 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(C)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N1(C2CCCCC=2)CCCC1.[OH2:29]>>[CH2:1]([CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C:11]1=[O:29])[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 707681-Pyrrolidino-1-cyclohexene

Product 1

HCID 105128992-(2-Oxo-2-phenylethyl)cyclohexanone

Procedure

A solution of 60.9 g (0.31 mole) of phenacyl bromide in 150 ml. of toluene was added dropwise with stirring to a refluxing solution of 46.6 g. of 1-pyrrolidino-1-cyclohexene in 150 ml. of toluene. The mixture was heated under reflux for 2 hours, diluted with 150 ml. of water, refluxed for 3 hours and cooled. The layers were separated, and the aqueous phase was extracted with ether. The organic solution was dried and concentrated to an oil. Distillation gave 42.1 g. (64%) of orange liquid, b.p. 135°-141° (0.05 mm.), which solidified. Recrystallization from ether-petroleum ether gave tan crystals, m.p. 44°-45°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. additiondiluted with 150 ml
  4. temperaturecooled
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with ether
  7. customThe organic solution was dried
  8. concentrationconcentrated to an oil
  9. distillationDistillation
  10. customgave 42.1 g
  11. customRecrystallization from ether-petroleum ether
  12. customgave tan crystals, m.p. 44°-45°

Sources & evidence

ORD record
ord-42928761a957422d8773171886439eb0
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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