Hydrochloric Acid → 4-Hydroxy-2-methoxybenzoic acid

HRID 2230722Notes

Reaction equation

HRID 2230722 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.[OH-].[Na+].Cl>>[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Product 1

HCID 126955754-Hydroxy-2-methoxybenzoic acidYield 101.1%

Procedure

Stir a mixture of methyl 4-hydroxy-2-methoxybenzoate (Danishefsky et al., J. Med. Chem. 1979, 101, 7001-7008, 0.37 g, 2 mmol) and 1N NaOH for two hours at room temperature. Acidify 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 overnight to afford 4-hydroxy-2-methoxybenzoic acid (0.34 g).

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 overnight

Sources & evidence

ORD record
ord-50091bdbefe84762b7fb2abfa144d2b9
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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