Potassium Hydroxide → 2-Chloro-3,5-dimethoxybenzoic acid

HRID 1783546Notes

Reaction equation

HRID 1783546 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[C:6]([O:12][CH3:13])[C:5]=1[Cl:14].[OH-].[K+]>CO>[Cl:14][C:5]1[C:6]([O:12][CH3:13])=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:4]=1[C:3]([OH:15])=[O:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 536694802-Chloro-3,5-dimethoxy-benzoic acid methyl ester

Product 1

HCID 543612282-Chloro-3,5-dimethoxybenzoic acidYield 87.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of 12 g (52.0 mmol) of 2-chloro-3,5-dimethoxy-benzoic acid methyl ester (prepared according to the method of T. R. Kasturi and E. M. Abraham, Indian Journal of Chemistry, 1973; 11:1099-1104) in 40 mL of methanol was added 60 mL (60 mmol) of 1N potassium hydroxide solution. After stirring overnight at room temperature, the methanol was removed in vacuo, and the residue was suspended in 800 mL of water. The aqueous layer was extracted three times with diethyl ether and the acidified with concentrated hydrochloric acid to a pH of 3. The resulting white solid was filtered, washed well with water, and air-dried to give 9.82 g (87%) of the title compound.

Workup

  1. customthe methanol was removed in vacuo
  2. extractionThe aqueous layer was extracted three times with diethyl ether
  3. filtrationThe resulting white solid was filtered
  4. washwashed well with water
  5. customair-dried

Sources & evidence

ORD record
ord-71d7361537f840fea2093b24cf35b4c3
Source dataset
uspto-grants-2009_03
Patent number
US07501425B1

Reaction notes

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