Water → Cyclohexanone, 2-[2-(4-bromophenyl)-2-oxoethyl]-

HRID 1973456Notes

Reaction equation

HRID 1973456 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.[C:12]1(C)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1(C2CCCCC=2)CCCC1.[OH2:30]>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]2=[O:30])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1140Toluene2×HCID 74544-Bromophenacyl bromideHCID 707681-Pyrrolidino-1-cyclohexene

Product 1

HCID 12270330Cyclohexanone, 2-[2-(4-bromophenyl)-2-oxoethyl]-

Procedure

A suspension of 50 g (0.18 mole) of p-bromophenacyl bromide in 215 ml. of toluene is added in small portions to a stirred boiling solution of 27.2 g (0.18 mole) of 1-pyrrolidino-1-cyclohexene in 90 ml. of toluene. The mixture is heated under reflux for 2 hours, diluted with 90 ml. of water and refluxed for 3 hours. The layers are separated and the aqueous phase is extracted with ether. The organic solution is dried over sodium sulfate and concentrated to an oil which solidifies. The solid is recrystallized from a cyclohexane-ethanol mixture to give 2-(p-bromophenacyl)-cyclohexanone as colorless crystals, m.p. 78°-80° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 2 hours
  3. additiondiluted with 90 ml
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted with ether
  6. dry with materialThe organic solution is dried over sodium sulfate
  7. concentrationconcentrated to an oil which
  8. customThe solid is recrystallized from a cyclohexane-ethanol mixture

Sources & evidence

ORD record
ord-2e639a9348ad4c82a41a95c86382af2d
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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