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

HRID 1973454Notes

Reaction equation

HRID 1973454 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 is added dropwise with stirring to a refluxing solution of 46.6 g of 1-pyrrolidino-1-cyclohexene in 150 ml. of toluene. The mixture is heated under reflux for 2 hours, diluted with 150 ml. of water, refluxed for 3 hours and cooled. The layers are separated and the aqueous phase is extracted with ether. The organic solution is dried and concentrated to an oil. The oil is distilled to give an orange liquid which solidifies. The resulting solid is recrystallized from an ether petroleum mixture to give 2-phenacylcyclohexanone as tan crystals, m.p. 44°-45° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. additiondiluted with 150 ml
  4. temperaturecooled
  5. customThe layers are separated
  6. extractionthe aqueous phase is extracted with ether
  7. customThe organic solution is dried
  8. concentrationconcentrated to an oil
  9. distillationThe oil is distilled
  10. customto give an orange liquid which
  11. customThe resulting solid is recrystallized from an ether petroleum mixture

Sources & evidence

ORD record
ord-796893c570124ef8a939315e78f79dd1
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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