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

HRID 26619Notes

Reaction equation

HRID 26619 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-26a2cdde76624980b19243533ed01893
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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