Water → Cyclohexanone, 2-[2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl]-

HRID 1579870Notes

Reaction equation

HRID 1579870 reaction equation
N1([C:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]=2)CCCC1.[F:12][C:13]([F:25])([F:24])[C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17](=[O:20])[CH2:18]Br.C1(C)C=CC=CC=1.[OH2:33]>>[F:12][C:13]([F:25])([F:24])[C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17](=[O:20])[CH2:18][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][C:6]1=[O:33]

Participants

5

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 707681-Pyrrolidino-1-cyclohexeneHCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-one

Product 1

HCID 12270334Cyclohexanone, 2-[2-oxo-2-[3-(trifluoromethyl)phenyl]ethyl]-

Procedure

A stirred mixture of 15.9 g. (0.11 mole) of 1-pyrrolidino-1-cyclohexene, 28.0 g. (0.11 mole) of m-trifluoromethylphenacyl bromide, and 100 ml. of toluene was heated under reflux for 2 hours, diluted with water and refluxed for 2 hours. The layers were separated, and the organic phase was dried and concentrated to 25 g. of liquid. Distillation provided 12.0 g. (42%) of liquid, b.p. 137°-138° (0.075 mm.).

Workup

  1. additionA stirred mixture of 15.9 g
  2. temperatureunder reflux for 2 hours
  3. temperaturerefluxed for 2 hours
  4. customThe layers were separated
  5. customthe organic phase was dried
  6. concentrationconcentrated to 25 g
  7. distillationDistillation
  8. customprovided 12.0 g

Sources & evidence

ORD record
ord-6c0dc12d773e4157afd16ddf5bfc3fdf
Source dataset
uspto-grants-1976_01
Patent number
US03931407

Reaction notes

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