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

HRID 1462632Notes

Reaction equation

HRID 1462632 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 was added 300 g (4.6 mole) of activated zinc dust and 100 g (0.42 mole) 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. 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 with mp 142°-144°.

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 with mp 142°-144°

Sources & evidence

ORD record
ord-6b0542dc8f094146a07e377d9c9cdea2
Source dataset
uspto-grants-1984_07
Patent number
US04460781

Reaction notes

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