Acetic Anhydride → Acetoxy-(4-bromo-phenyl)-acetic acid

HRID 1714161Notes

Reaction equation

HRID 1714161 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]([OH:10])[C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>N1C=CC=CC=1>[C:13]([O:10][CH:6]([C:5]1[CH:11]=[CH:12][C:2]([Br:1])=[CH:3][CH:4]=1)[C:7]([OH:9])=[O:8])(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 97930p-Bromomandelic acid

Product 1

HCID 57820057Acetoxy-(4-bromo-phenyl)-acetic acidYield 75%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-bromomandelic acid (20.6 g, 89.0 mmol) dissolved in pyridine (50 mL) was added acetic anhydride (10 g, 98 mmol) dropwise while cooling with an ice bath. After stirring overnight at room temperature, the solvent was removed and the resulting residue dissolved in ethyl acetate (150 mL). This was washed twice with 1N HCl, brine, and then concentrated in vacuo to obtain a white solid (18.2 g, 75%) which was used without further purification.

Workup

  1. temperaturewhile cooling with an ice bath
  2. customthe solvent was removed
  3. dissolutionthe resulting residue dissolved in ethyl acetate (150 mL)
  4. washThis was washed twice with 1N HCl, brine
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-962feb44c0c64c72be222d6733f89755
Source dataset
uspto-grants-2010_09
Patent number
US07795315B2

Reaction notes

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