Methyl 4-amino-o-anisate → Methyl 4-hydroxy-2-methoxybenzoate

HRID 1872698Notes

Reaction equation

HRID 1872698 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7](N)=[CH:6][C:5]=1[O:11][CH3:12].N([O-])=[O:15].[Na+]>S(=O)(=O)(O)O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([OH:15])=[CH:6][C:5]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 168705Methyl 4-amino-o-anisateHCID 23668193Sodium Nitrite

Product 1

HCID 12532676Methyl 4-hydroxy-2-methoxybenzoateYield 64.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

4-Amino-2-methoxy benzoic acid methyl ester (15 g, 82.7 mmol) was dissolved in sulfuric acid (80 ml of a 25% solution). The solution was cooled in an ice bath and diazotized with saturated sodium nitrite solution (8.57 g, 124 mmol) maintaining the temperature below 5° C. The diazonium solution was poured slowly into boiling sulphuric acid (1L of a 3% solution) and the mixture was heated for an additional 5 mins. The mixture was then allowed to cool before being extracted with dichloromethane. The organic extracts were combined, dried over sodium sulfate and concentrated in vacuo to afford a brown solid (9.7 g).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. temperaturemaintaining the temperature below 5° C
  3. temperaturewas heated for an additional 5 mins
  4. temperatureto cool
  5. extractionbefore being extracted with dichloromethane
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-354eb511755a4af699723c79a21fc836
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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