2-Bromo-4'-(trifluoromethyl)acetophenone → 2-Hydroxy-1-[4-(trifluoromethyl)phenyl]ethan-1-one

HRID 747463

Reaction equation

HRID 747463 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=[O:4].C([O-])=[O:16].[Na+]>CO>[OH:16][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 2723810Sodium Formate

Product 1

HCID 112871692-Hydroxy-1-[4-(trifluoromethyl)phenyl]ethan-1-oneYield 80.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-bromo-4′-trifluoromethyl acetophenone (40.0 g), sodium formate (40.0 g) and methanol (200 ml) was stirred with heating under reflux for 6 hours. The reaction mixture was concentrated and poured into water (500 ml). The precipitated crystals were filtered, washed with water, and air-dried to give crystals of 2-hydroxy-4′-trifluoromethyl acetophenone (24.5 g, 80%). Melting point 112-114° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionpoured into water (500 ml)
  5. filtrationThe precipitated crystals were filtered
  6. washwashed with water
  7. customair-dried

Sources & evidence

ORD record
ord-f61f4db1f4544df8b5e358bd42ac7ac6
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Linked notes

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