P-Chloroacetophenone → 1-(4-Chlorophenyl)-1-phenylethan-1-ol

HRID 652975Notes

Reaction equation

HRID 652975 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=1.[Cl-].[NH4+]>O1CCCC1>[C:1]1([C:16]([C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)([OH:18])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7467P-ChloroacetophenoneHCID 25517Ammonium ChlorideHCID 178418255HCID 178418255, compound

Product 1

HCID 141899961-(4-Chlorophenyl)-1-phenylethan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 37 ml of a 2M solution of phenylmagnesium bromide in tetrahydrofuran was added, under argon atmosphere, 5.24 g (33.9 mmol) of p-chloroacetophenone, and the mixture was allowed to react at 0° C. for 3 hours. At the completion of this reaction, a saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with chloroform. The organic layer was washed with water and then concentrated by evaporation under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with chloroform, to give 6.99 g (30.0 mmol) of 1-phenyl-1-(p-chlorophenyl)ethanol. To a solution of 6.99 g (30.0 mmol) of the alcohol compound in ethanol (80 ml) was added 5.00 ml (93.8 mmol) of conc. sulfuric acid, and the mixture was reacted for 1 hour.

Workup

  1. customto react at 0° C. for 3 hours
  2. customAt the completion of this reaction
  3. extractionwas then extracted with chloroform
  4. washThe organic layer was washed with water
  5. concentrationconcentrated by evaporation under reduced pressure
  6. washeluted with chloroform

Sources & evidence

ORD record
ord-9e16b91106074747ad353de2d0796740
Source dataset
uspto-grants-1987_06
Patent number
US04673684

Reaction notes

Loading…