Hydrochloric Acid → 4-Chloro-2-ethoxybenzoic acid

HRID 2263924Notes

Reaction equation

HRID 2263924 reaction equation
C([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[O:12][CH2:13][CH3:14])C.[OH-].[K+].Cl>C(O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:15])=[O:3])=[C:6]([O:12][CH2:13][CH3:14])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 22494013HCID 22494013, compound

Product 1

HCID 189546044-Chloro-2-ethoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-2-ethoxybenzoic acid ethyl ester (˜18 g) was suspended in ethanol (500 mL). This was treated with potassium hydroxide (200 mL, 2 M solution) and refluxed for 1 h. The reaction was cooled and poured into cold aqueous hydrochloric acid (300 mL, 3 M solution) and extracted into dichloromethane (3×500 mL). The dichloromethane was washed with water (500 mL) and dried over magnesium sulfate and evaporated to dryness to give 4-chloro-2-ethoxy-benzoic acid as a solid.

Workup

  1. temperaturerefluxed for 1 h
  2. temperatureThe reaction was cooled
  3. extractionextracted into dichloromethane (3×500 mL)
  4. washThe dichloromethane was washed with water (500 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-9c58656b0d23494e85f970f2bc75b7fe
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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