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

HRID 1598703Notes

Reaction equation

HRID 1598703 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 2N 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-22df3c0b35ef4e33824db89ee6b0428f
Source dataset
uspto-grants-1998_04
Patent number
US05739128

Reaction notes

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