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

HRID 1939182Notes

Reaction equation

HRID 1939182 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 1N 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-23d3fa556d04493c95ec7993a73738f5
Source dataset
uspto-grants-1997_12
Patent number
US05696112

Reaction notes

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