2-Benzoyl-4-chlorobenzoic acid → 2-Benzyl-4-chlorobenzoic acid

HRID 1903613Notes

Reaction equation

HRID 1903613 reaction equation
[C:1]([C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[OH-].[NH4+].[Zn]>[CH2:1]([C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 122052902-Benzoyl-4-chlorobenzoic acid

Product 1

HCID 130670812-Benzyl-4-chlorobenzoic acid

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 14923Ammonium HydroxideSolvent2×

Procedure

To a solution of 5.0 g of cupric sulfate in 3 liters of concentrated ammonium hydroxide solution were added 300 g (4.6 mol) of activated zinc dust and 100 g (0.42 mol) of 2-benzoyl-4-chlorobenzoic acid. The mixture was refluxed for 3 days, during which the volume was maintained by the addition of concentrated ammonium hydroxide solution. The mixture was cooled, and the excess zinc was removed by filtration. The filtrate was acidified by the addition of concentrated hydrochloric acid to a pH of 3. The resulting precipitate was collected by filtration and dried to constant weight to give a white solid, mp 142°-144° C.

Workup

  1. temperatureThe mixture was refluxed for 3 days, during which the volume
  2. temperatureThe mixture was cooled
  3. customthe excess zinc was removed by filtration
  4. additionThe filtrate was acidified by the addition of concentrated hydrochloric acid to a pH of 3
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried to constant weight
  7. customto give a white solid, mp 142°-144° C.

Sources & evidence

ORD record
ord-14af89d308054eb08698427c91271906
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

Loading…