Hydrochloric Acid → 2-Methoxy-5-(2-methoxy-ethoxy)-benzoic acid

HRID 2230726Notes

Reaction equation

HRID 2230726 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])[CH:7]=[CH:6][C:5]=1[O:15][CH3:16].[OH-].[Na+].Cl>CO>[CH3:16][O:15][C:5]1[CH:6]=[CH:7][C:8]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[CH:9][C:4]=1[C:3]([OH:17])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 701476262-Methoxy-5-(2-methoxy-ethoxy)-benzoic acid methyl ester

Product 1

HCID 184648502-Methoxy-5-(2-methoxy-ethoxy)-benzoic acidYield 100.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir a mixture of 2-methoxy-5-(2-methoxy-ethoxy)-benzoic acid methyl ester (0.87 g, 3.6 mmol), methanol (20 mL) and 1N NaOH solution (20 mL) for two hours at room temperature. Acidify the reaction with 1N HCl and extract with dichloromethane. Dry (MgSO4) the organic phase, filter and concentrate the filtrate in vacuo. Vacuum dry the residue at room temperature over 48 hours to afford 0.82 g of 2-methoxy-5-(2-methoxy-ethoxy)-benzoic acid as an oil, Rf=0.84 (silica gel, dichloromethane:methanol:acetic acid, 85:10:5).

Workup

  1. extractionextract with dichloromethane
  2. dry with materialDry (MgSO4) the organic phase
  3. filtrationfilter
  4. concentrationconcentrate the filtrate in vacuo
  5. customVacuum dry the residue at room temperature over 48 hours

Sources & evidence

ORD record
ord-ecb1a8568090486ca1c2019c5a320fe5
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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