Potassium Hydroxide → 2-(Carboxymethoxy)-4-chlorobenzoic acid

HRID 1403372Notes

Reaction equation

HRID 1403372 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([O:12][CH2:13][C:14]([O:16]CC)=[O:15])[CH:3]=1.[OH-].[K+]>CO.O>[C:14]([CH2:13][O:12][C:4]1[CH:3]=[C:2]([Cl:1])[CH:11]=[CH:10][C:5]=1[C:6]([OH:8])=[O:7])([OH:16])=[O:15]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 70665052Methyl 4-chloro-2-(2-ethoxy-2-oxoethoxy)benzoate

Product 1

HCID 137781362-(Carboxymethoxy)-4-chlorobenzoic acidYield 82.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 4-chloro-2-(2-ethoxy-2-oxoethoxy)benzoate (10 g, 36.67 mmol) in methanol (250 mL) and water (50 mL) was added potassium hydroxide (4 g, 71.43 mmol). After stirring for 1.5 h at 25° C., the resulting mixture was concentrated under vacuum, dissolved in water (50 mL), adjusted to pH 6 with HCl (3N) and filtered to give 2-(carboxymethoxy)-4-chlorobenzoic acid as a white solid (7 g, 80%).

Workup

  1. concentrationthe resulting mixture was concentrated under vacuum
  2. dissolutiondissolved in water (50 mL)
  3. filtrationfiltered

Sources & evidence

ORD record
ord-ccb8e148a496439d9c901108651d162e
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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