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

HRID 1579869Notes

Reaction equation

HRID 1579869 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 was 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 was heated under reflux for 2 hours, diluted with 90 ml. of water, and refluxed for 3 hours. The layers were separated and the aqueous phase was extracted with ether. The organic solution was dried over sodium sulfate and concentrated to an oil which solidified. Recrystallization from cyclohexane-ethanol gave 19.8 g. (37%) of colorless crystals, m.p. 78°-80°.

Workup

  1. additionA suspension of 50 g
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. additiondiluted with 90 ml
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with ether
  7. dry with materialThe organic solution was dried over sodium sulfate
  8. concentrationconcentrated to an oil which
  9. customRecrystallization from cyclohexane-ethanol
  10. customgave 19.8 g

Sources & evidence

ORD record
ord-25c2cea5d43f46b2b7a0c2cdff45c012
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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