Hydrogen Bromide → (4-Hydroxy-3-methylphenyl)(phenyl)methanone

HRID 249281Notes

Reaction equation

HRID 249281 reaction equation
C[O:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:17].Br>C(O)(=O)C>[CH3:17][C:4]1[CH:5]=[C:6]([CH:15]=[CH:16][C:3]=1[OH:2])[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 115141104-Methoxy-3-methylbenzophenone

Product 1

HCID 219245(4-Hydroxy-3-methylphenyl)(phenyl)methanoneYield 50.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6.17 g of 4-methoxy-3-methylbenzophenone, 65 ml of glacial acetic acid and 103 ml of a 62 percent hydrobromic acid solution is heated to boiling under reflux for 3 hours. The dark solution obtained is concentrated, extracted with ethyl acetate and the organic phase is dried and evaporated. The residue is chromatographed on silica gel with hexane:ethyl acetate (7:3). There are obtained 2.90 g (50%) of 3-methyl-4-hydroxybenzophenone as a yellowish solid with a m.p. of 170°-173° .

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. customThe dark solution obtained
  4. concentrationis concentrated
  5. extractionextracted with ethyl acetate
  6. customthe organic phase is dried
  7. customevaporated
  8. customThe residue is chromatographed on silica gel with hexane:ethyl acetate (7:3)

Sources & evidence

ORD record
ord-efda8b0d8e5a4d5c92157373fd8f01cb
Source dataset
uspto-grants-1993_05
Patent number
US05214046

Reaction notes

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