Hydrochloric Acid → 4-Chloro-2-ethoxybenzoic acid

HRID 1816657Notes

Reaction equation

HRID 1816657 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=[O:7])=[C:4]([O:13][CH2:14][CH3:15])[CH:3]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:13][CH2:14][CH3:15])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22494013HCID 22494013, compound

Product 1

HCID 189546044-Chloro-2-ethoxybenzoic acidYield 114%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.2 g of ethyl 4-chloro-2-ethoxybenzoate was dissolved in 5 ml methanol, and 2 ml of 1N sodium hydroxide was added, and the mixture was stirred at room temperature for 6 hours. The reaction mixture was ice-cooled and neutralized with 1N hydrochloric acid, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was evaporated, to give 0.20 g of 4-chloro-2-ethoxybenzoic acid.

Workup

  1. temperaturecooled
  2. extractionby extracting with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b580a21dbd5747b68735a613481df975
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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