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

HRID 1030673Notes

Reaction equation

HRID 1030673 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. temperatureunder reflux for 3 hours
  2. customThe dark solution obtained
  3. concentrationis concentrated
  4. extractionextracted with ethyl acetate
  5. customthe organic phase is dried
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with hexane:ethyl acetate (7:3)

Sources & evidence

ORD record
ord-d9d4ce81c1f149ff8a34d74d02c871d1
Source dataset
uspto-grants-1992_04
Patent number
US05106878

Reaction notes

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