Acetic Acid → [4-(2-Bromoethyl)phenyl]acetic acid

HRID 46986Notes

Reaction equation

HRID 46986 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7](CC#N)=[CH:6][CH:5]=1.[C:13]([OH:16])(=[O:15])[CH3:14]>Br>[Br:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:14][C:13]([OH:16])=[O:15])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 20386067HCID 20386067, compound

Product 1

HCID 20386065[4-(2-Bromoethyl)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of [4-(2-bromoethyl)phenyl]acetonitrile (56.0 g., 0.25 mole) in 48% hydrobromic acid (200 ml.) and acetic acid (600 ml.) is boiled under reflux for 4 hours. The solution is reduced to one-third volume by distillation at reduced pressure. The residue is diluted with 400 ml. of water to force out the oily product which is taken up in ether, washed with water, and dried over sodium sulfate. Evaporation of the solvent leaves the title compound as a residual oil.

Workup

  1. temperatureunder reflux for 4 hours
  2. distillationThe solution is reduced to one-third volume by distillation at reduced pressure
  3. additionThe residue is diluted with 400 ml
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4e41ede932f44fa7b8b63fc60f92d7ac
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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