Hydrogen Bromide → 3-Hydroxybenzophenone

HRID 877342Notes

Reaction equation

HRID 877342 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.Br.CCOC(C)=O>CC(O)=O>[OH:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 8857Ethyl AcetateHCID 12451863(3-Methoxyphenyl)(phenyl)methanone

Product 1

HCID 830503-HydroxybenzophenoneYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

1458 g (6.9 mol) of (3-methoxyphenyl)(phenyl)methanone was dissolved in 2090 mL of AcOH. To the solution, 2320 ml (20.6 mol) of 48% HBr was added and the mixture was stirred at 90° C. for 18 hours. The reaction was monitored by TLC (AcOEt:hex 1:9). After reaction was completed the mixture was cooled down to RT and poured into ice with stirring. The precipitated solid was filtered, washed with water and dried yielding the title compound as a white solid (1234 g, 91%).

Workup

  1. customAfter reaction
  2. temperaturewas cooled down to RT
  3. additionpoured into ice
  4. stirringwith stirring
  5. filtrationThe precipitated solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-09b1192e5f4e462c8943dcb322ea8fd5
Source dataset
uspto-grants-2015_03
Patent number
US08987299B2

Reaction notes

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