Citric Acid → 4-[2-(2-Chlorophenyl)-2-oxoethyl]benzoic acid

HRID 1739940Notes

Reaction equation

HRID 1739940 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:20])[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][CH:11]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:20])[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 21837116Methyl 4-[2-(2-chlorophenyl)-2-oxoethyl]benzoate

Product 1

HCID 218371444-[2-(2-Chlorophenyl)-2-oxoethyl]benzoic acidYield 96.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 18.78 g of methyl 4-[2-(2-chlorophenyl)-2-oxoethyl]benzoate in 288.8 ml of CH3OH, 72.2 ml of water and 5.2 g of NaOH is refluxed for 3 hours then acidified with 2 N citric acid. The reaction mixture is evaporated in vacuo to remove the CH3OH. The aqueous phase is extracted with CH2Cl2 and acidified with 1 N HCl. The resulting solid is collected and dried under vacuum to give 17.27 g of the desired product, m.p. 168-172° C.

Workup

  1. temperatureis refluxed for 3 hours
  2. customThe reaction mixture is evaporated in vacuo
  3. customto remove the CH3OH
  4. extractionThe aqueous phase is extracted with CH2Cl2
  5. customThe resulting solid is collected
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b7b447b78eb54857a6ae55d8d096c7dc
Source dataset
uspto-grants-1999_10
Patent number
US05968937

Reaction notes

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