Methanol → Methyl 3-amino-4-hydroxybenzoate

HRID 551808Notes

Reaction equation

HRID 551808 reaction equation
CO.[C:3](Cl)(=O)C.[NH2:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[OH:17])[C:11]([OH:13])=[O:12].C(=O)([O-])O.[Na+]>O>[NH2:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[OH:17])[C:11]([O:13][CH3:3])=[O:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 650833-Amino-4-hydroxybenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 10815Methyl 3-amino-4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 ml of methanol are introduced into a 500 ml three-necked flask and then, at 0° C., 9.75 ml of acetyl chloride are added dropwise. 5 g of 3-amino-4-hydroxybenzoic acid are subsequently added at 0° C. and then the reaction medium is stirred at ambient temperature for eighteen hours. A saturated solution of sodium hydrogencarbonate in water is subsequently added at 0° C. and the mixture is extracted three times with ethyl acetate. The organic phases are combined and then dried over magnesium sulfate and the solvent is evaporated under reduced pressure to result in 5.16 g of methyl 3-amino-4-hydroxybenzoate.

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent is evaporated under reduced pressure
  4. customto result in 5.16 g of methyl 3-amino-4-hydroxybenzoate

Sources & evidence

ORD record
ord-2e9b834bf1244a7dbcb3085b15fa46cd
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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