Hydrochloric Acid → 2-Propoxybenzoic acid

HRID 1063900Notes

Reaction equation

HRID 1063900 reaction equation
[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9]C)=[O:8])[CH2:2][CH3:3].[OH-].[Na+].Cl>CO>[CH2:1]([O:4][C:5]1[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([OH:9])=[O:8])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11084741Methyl 2-propoxybenzoate

Product 1

HCID 5392152-Propoxybenzoic acidYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-(propyloxy)benzoate (841 mg) in methanol (20 ml) was added 2N sodium hydroxide solution (5 ml) and the mixture was stirred at 60° C. for 2 hours. The reaction mixture was acidified with 6N hydrochloric acid to pH 4 and organic solvent was removed by evaporation. The aqueous layer was diluted with water and extracted with chloroform. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo to give 2-(propyloxy)benzoic acid as colorless oil (756 mg).

Workup

  1. customwas removed by evaporation
  2. additionThe aqueous layer was diluted with water
  3. extractionextracted with chloroform
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-56a5c324676a4d0897f0aba5a1cacc35
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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