2-Bromo-1-(4-hydroxyphenyl)ethanone → Cyclohexanone, 2-[2-(4-hydroxyphenyl)-2-oxoethyl]-

HRID 1973459Notes

Reaction equation

HRID 1973459 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.N1([C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=2)CCCC1.CN(C)C=[O:26]>O>[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][C:17]2=[O:26])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 6228DimethylformamideHCID 707681-Pyrrolidino-1-cyclohexene

Product 1

HCID 12270333Cyclohexanone, 2-[2-(4-hydroxyphenyl)-2-oxoethyl]-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

43 g (0.2 mole) of (p-hydroxyphenacyl bromide) are added dropwise during 1/2 hour to a cooled (25° C) solution of 30 g (0.2 mole) of 1-pyrrolidino-1-cyclohexene in dimethylformamide. After 51/2 hours, the solution is diluted with water and extracted with chloroform. The chloroform solution is washed with water, dried over sodium sulfate and concentrated to an oil. Distillation gives a liquid which solidifies to give 2-(p-hydroxyphenacyl) cyclohexanone, m.p. 120°-125° C.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform solution is washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to an oil
  5. distillationDistillation
  6. customgives a liquid which

Sources & evidence

ORD record
ord-b4dfb3d234594e2184b03bf3ea2e986a
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

Loading…