4,4'-Dimethoxybenzil → 4,4'-Dihydroxybenzil

HRID 530417

Reaction equation

HRID 530417 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=2)=[O:12])=[O:10])=[CH:5][CH:4]=1>Br.CC([O-])=O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:10])[C:11]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)=[O:12])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 710434,4'-Dimethoxybenzil

Product 1

HCID 4582044,4'-DihydroxybenzilYield 105.9%

Reagents, catalysts & solvents 2

HCID 175AcetateSolventHCID 260Hydrogen BromideSolvent

Procedure

4,4′-dimethoxybenzil (2.0 g, 7.41 mmol) was dissolved in 30 mL of hydrogen bromide and 10 mL of acetic acid glacial. The reaction was stirred at reflux temperature overnight. The mixture was extracted with ethyl acetate and the organic phase was washed with water, dried over sodium sulphate. Concentration under vaccum gave the title compound as a yellow solid (1.9 g, quantitative).

Workup

  1. temperatureat reflux temperature overnight
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationConcentration under vaccum

Sources & evidence

ORD record
ord-4a62e416177a4f4ebd82c7f82b8a06e7
Source dataset
uspto-grants-2016_05
Patent number
US09353089B2

Linked notes

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