Sodium Hydroxide → 3-Chlorophenylglyoxylic acid

HRID 716732Notes

Reaction equation

HRID 716732 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([C:10](=[O:16])[C:11]([O:13]CC)=[O:12])[CH:7]=[CH:8][CH:9]=1>C1COCC1.CO>[Cl:3][C:4]1[CH:5]=[C:6]([C:10](=[O:16])[C:11]([OH:13])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2758814ethyl 2-(3-chlorophenyl)-2-oxoacetate

Product 1

HCID 122529103-Chlorophenylglyoxylic acidYield 115.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

An aqueous 2 mol/L NaOH solution (24 mL) was added to a solution of ethyl (3-chlorophenyl)(oxo)acetate (2.00 g) in THF/MeOH (1:1) (48 mL) in an ice bath, followed by stirring at room temperature overnight. The solvent was distilled off under reduced pressure, and an aqueous 3 mol/L HCl solution was added thereto in an ice bath. The precipitated solid was collected by filtration to yield the title compound (2.00 g, colorless solid).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionan aqueous 3 mol/L HCl solution was added
  3. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-ed40ffaa3da34e729845a2fd9b3e881b
Source dataset
uspto-grants-2015_11
Patent number
US09193695B2

Reaction notes

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