Hydrogen Bromide → 4,4'-Dihydroxybenzil

HRID 2179480Notes

Reaction equation

HRID 2179480 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.O>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)=[O:12])=[O:10])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 962WaterHCID 710434,4'-Dimethoxybenzil

Product 1

HCID 4582044,4'-Dihydroxybenzil

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

4,4′-Dimethoxybenzil (5.0 g) was dissolved in acetic acid (95 mL). To the solution, 48 mass % aqueous HBr (31.2 g) was added dropwise at 70° C. over 10 minutes. After addition of HBr, the mixture was stirred at 110° C. for 70 hours. Subsequently, water (150 g) was added to the mixture, to thereby crystallize the product. The crude crystals were recovered through filtration and washed with water (250 g), followed by drying, to thereby yield 4.0 g of 4,4′-dihydroxybenzil as a target product.

Workup

  1. customto thereby crystallize the product
  2. filtrationThe crude crystals were recovered through filtration
  3. washwashed with water (250 g)
  4. customby drying

Sources & evidence

ORD record
ord-08a205cc1da54447bde273c70fcec6c1
Source dataset
uspto-grants-2015_06
Patent number
US09068024B2

Reaction notes

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