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

HRID 2279687Notes

Reaction equation

HRID 2279687 reaction equation
[C:1]1([C:9]([C:11]([C:13]2[CH:20]=[CH:19][C:16]([O:17]C)=[CH:15][CH:14]=2)=[O:12])=[O:10])[CH:8]=[CH:7][C:4]([O:5]C)=[CH:3][CH:2]=1>C(O)(=O)C.Br>[OH:5][C:4]1[CH:3]=[CH:2][C:1]([C:9]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([OH:17])=[CH:19][CH:20]=2)=[O:12])=[O:10])=[CH:8][CH:7]=1

Participants

4

Reactant 1

HCID 710434,4'-Dimethoxybenzil

Product 1

HCID 4582044,4'-DihydroxybenzilYield 97%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

12 g of anisil was dissolved in 120 ml of acetic acid and 240 ml of 48% hydrobromic acid. The mixture was stirred vigorously and heated to reflux to for 4 hours. The temperature was then lowered to 90° C. and left overnight. The resulting solution was poured over ice and the precipitate was collected by filtration and washed with water. After drying, 10.43 g of product (yield: 75.0 mol %) with a purity of 76.8% was obtained. The purity was measured by gas chromatography.

Workup

  1. temperatureheated
  2. temperatureto reflux to for 4 hours
  3. customwas then lowered to 90° C.
  4. additionThe resulting solution was poured over ice
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customAfter drying

Sources & evidence

ORD record
ord-386eab3149fc46dc9099ed22a546ad30
Source dataset
uspto-grants-2015_09
Patent number
US09133320B2

Reaction notes

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