Benzil, 4-methoxy- → Ethanedione, (4-hydroxyphenyl)phenyl-

HRID 436386Notes

Reaction equation

HRID 436386 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][CH:16]=[CH:15][CH:14]=2)=[O:12])=[O:10])=[CH:5][CH:4]=1>C(O)(=O)C.Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:12])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 31494Benzil, 4-methoxy-

Product 1

HCID 142278Ethanedione, (4-hydroxyphenyl)phenyl-Yield 64%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 50 g (0.21 mole) of 4-methoxybenzil in 250 ml of acetic acid and 300 ml of 48% hydrobromic acid was heated to reflux for 10 hours. A solid that separated on cooling was recovered by filtration and the filtrate extracted with ether. The solid was dissolved in ether, the ether solutions combined and extracted with 10 % potassium hydroxide. The potassium hydroxide solution was washed with ether and neutralized with hydrochloric acid. The resulting solid was dissolved in ether, the solution dried over magnesium sulfate, and the ether removed by distillation. The resulting dark, brown solid was recrystallized from benzene to yield 30 g (64%) of 4-hydroxybenzil; mp, 138°-140°, lit., 129°-130°.

Workup

  1. temperatureto reflux for 10 hours
  2. customA solid that separated
  3. temperatureon cooling
  4. filtrationwas recovered by filtration
  5. extractionthe filtrate extracted with ether
  6. dissolutionThe solid was dissolved in ether
  7. extractionextracted with 10 % potassium hydroxide
  8. washThe potassium hydroxide solution was washed with ether and neutralized with hydrochloric acid
  9. dissolutionThe resulting solid was dissolved in ether
  10. dry with materialthe solution dried over magnesium sulfate
  11. customthe ether removed by distillation
  12. customThe resulting dark, brown solid was recrystallized from benzene

Sources & evidence

ORD record
ord-1ee3d897b8344d54a925ab5f54df1920
Source dataset
uspto-grants-1977_02
Patent number
US04009040

Reaction notes

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