Hydrogen Bromide → 4,4'-Dihydroxybenzil

HRID 1654249

Reaction equation

HRID 1654249 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>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

4

Reactant 2

HCID 260Hydrogen BromideHCID 710434,4'-Dimethoxybenzil

Product 1

HCID 4582044,4'-Dihydroxybenzil

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4,4'-Dimethoxybenzil (10 g), 90 ml glacial acetic acid and 160 ml 48% HBr were heated at reflux for 4 hours. The reaction mixture was poured into ice and the product collected by filtration. Dissolution of the solid into 10% aqueous sodium hydroxide, extraction with diethyl ether and acidification of the aqueous layer gave 4,4'-dihydroxybenzil which was recrystallized from 75% ethanol. Yield 7.5 g (84%). 1H NMR (acetone-d6) δ9.53 (s,2H, OH), 7.81, 6.98 (m, 8H, aromatic).

Workup

  1. temperatureat reflux for 4 hours
  2. additionThe reaction mixture was poured into ice
  3. filtrationthe product collected by filtration
  4. dissolutionDissolution of the solid
  5. extractioninto 10% aqueous sodium hydroxide, extraction with diethyl ether and acidification of the aqueous layer

Sources & evidence

ORD record
ord-a25754a942544d5fa2213559fada7256
Source dataset
uspto-grants-1995_04
Patent number
US05405926

Linked notes

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