Hydrogen Bromide → 3-Hydroxybenzophenone

HRID 874841Notes

Reaction equation

HRID 874841 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 this 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 the 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. temperaturewas cooled down to RT
  2. additionpoured into ice
  3. stirringwith stirring
  4. filtrationThe precipitated solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d9114ebbfeaa4bdaab1d16cb3f919887
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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