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

HRID 47936

Reaction equation

HRID 47936 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 heated under reflux and stirred for 16 h. The reaction mixture was concentrated and poured into water (1 L). The precipitated solid was collected by filtration, washed with water and then with isopropyl ether, air-dried, and further dried under reduced pressure at 40° C. to give the title compound as crystals (25.0 g, 42%). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 115-118° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. additionpoured into water (1 L)
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed with water
  7. dry with materialwith isopropyl ether, air-dried
  8. customfurther dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-3bf23ac72d0e454e87c0e21c7a1e4332
Source dataset
uspto-grants-2004_03
Patent number
US06699995B1

Linked notes

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