2-Bromo-1-(3,4-dichlorophenyl)ethanone → 1-(3,4-Dichlorophenyl)-2-hydroxyethan-1-one

HRID 747467

Reaction equation

HRID 747467 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=[O:4].C([O-])=[O:14].[Na+]>CO>[OH:14][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 2447512-Bromo-1-(3,4-dichlorophenyl)ethanoneHCID 2723810Sodium Formate

Product 1

HCID 70621931-(3,4-Dichlorophenyl)-2-hydroxyethan-1-oneYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-bromo-3′,4′-dichloroacetophenone (78.0 g), sodium formate (68.0 g) and methanol (300 ml) was stirred with heating under reflux for 16 hours. The reaction mixture was concentrated and poured into water (1 L). The solid precipitates were filtered, washed with water and then isopropyl ether, and air-dried. The residue was dried under reduced pressure to give crystals of 2-hydroxy-3′,4′-dichloroacetophenone (25.0 g, 42%). Recrystallization from ethyl acetate-hexane gave pale yellow prisms. Melting point 115-118° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 16 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionpoured into water (1 L)
  5. customThe solid precipitates
  6. filtrationwere filtered
  7. washwashed with water
  8. dry with materialisopropyl ether, and air-dried
  9. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-890678fea6054182989fef150ca76d42
Source dataset
uspto-grants-2008_07
Patent number
US07396848B1

Linked notes

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