Potassium Carbonate → Methyl 2-acetamido-3-hydroxybenzoate

HRID 1108697Notes

Reaction equation

HRID 1108697 reaction equation
[C:1]([NH:4][C:5]1[C:14]([O:15]C(=O)C)=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([NH:4][C:5]1[C:14]([OH:15])=[CH:13][CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 22627220Methyl 2-acetamido-3-acetoxybenzoate

Product 1

HCID 22627296Methyl 2-acetamido-3-hydroxybenzoateYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-acetamido-3-acetoxybenzoate (1.72 g) in methanol (9 ml) was added powdered potassium carbonate (1.4 g), and the mixture was stirred for 20 minutes. The resulting solid was removed by filtration and washed with methanol. The filtrate was evaporated in vacuo, and the residue was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was triturated with a mixture of isopropyl ether and hexane to give methyl 2-acetamido-3-hydroxybenzoate (1.21 g) as solid.

Workup

  1. customThe resulting solid was removed by filtration
  2. washwashed with methanol
  3. customThe filtrate was evaporated in vacuo
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was triturated with a mixture of isopropyl ether and hexane

Sources & evidence

ORD record
ord-225e37ea3c444009a4a3efc08272aa06
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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