2',3',4'-Trichloroacetophenone → 1-(2,3,4-Trichlorophenyl)ethan-1-ol

HRID 2396874Notes

Reaction equation

HRID 2396874 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:12])[CH3:11].[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=[CH:4][C:3]=1[CH:10]([OH:12])[CH3:11]

Participants

4

Reactant 2

HCID 261322',3',4'-TrichloroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 167691051-(2,3,4-Trichlorophenyl)ethan-1-olYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

In methanol (284 ml) is suspended 2',3',4'-trichloroacetophenone (94.7 g), and thereto is added sodium borohydride (7.6 g) at 15° C.-25° C. The mixture is stirred at 25° C. for two hours, and evaporated to remove the methanol. To the residue is added 2N hydrochloric acid (110 ml), and the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried, and evaporated to remove the solvent to give crude 1-(2,3,4-trichlorophenyl)ethanol (95 g).

Workup

  1. customevaporated
  2. customto remove the methanol
  3. additionTo the residue is added 2N hydrochloric acid (110 ml)
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe organic layer is washed with water
  6. customdried
  7. customevaporated
  8. customto remove the solvent

Sources & evidence

ORD record
ord-308a49edd35b4baa80ce56694a1619f2
Source dataset
uspto-grants-1996_02
Patent number
US05495012

Reaction notes

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