Methanol → Methyl 3-amino-4-hydroxybenzoate

HRID 2261100Notes

Reaction equation

HRID 2261100 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([NH2:1])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 650833-Amino-4-hydroxybenzoic acid

Product 1

HCID 10815Methyl 3-amino-4-hydroxybenzoateYield 95%

Conditions

Temperature
65 °C

Procedure

To a solution of 3-amino-4-hydroxybenzoic acid (10 g, 0.65 mol) in methanol (1.5 L) was added thionylchloride (233 g, 1.96 mol) drop-wise at 5-10° C. with stirring and allowed to reflux at 65° C. for 16 h. Excess methanol and thionylchloride was distilled off and crude dissolved in ethylacetate (500 mL). The organic layer was washed with 5% aqueous NaHCO3 solution, water, brine and dried. The solvent was removed under vacuum to give methyl-3-amino-4-hydroxybenzoate (105 g, 95%).

Workup

  1. distillationExcess methanol and thionylchloride was distilled off
  2. dissolutioncrude dissolved in ethylacetate (500 mL)
  3. washThe organic layer was washed with 5% aqueous NaHCO3 solution, water, brine
  4. customdried
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2f866d1fa9fe4b51904415db44b214de
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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