Hydrochloric Acid → Benzoic acid, 4-amino-3-hydroxy-, methyl ester

HRID 379021Notes

Reaction equation

HRID 379021 reaction equation
Cl.[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[OH:12].[CH3:13]O>>[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:13])=[O:8])=[CH:5][C:4]=1[OH:12]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1375664-Amino-3-hydroxybenzoic acid

Product 1

HCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

Conditions

Temperature
70 °C

Procedure

HCl (g) was bubbled through a solution of 4-amino-3-hydroxybenzoic acid (7 g, 54.8 mmol) in MeOH (450 mL) until saturated then the mixture was heated at 70° C. for 16 hr. The mixture was concentrated in vacuo, the residue taken up in EtOAc, washed with saturated NaHCO3 then brine and dried (MgSO4). Removal of the solvent yielded the title compound as a brown solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. washwashed with saturated NaHCO3
  3. dry with materialbrine and dried (MgSO4)
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-b4142f4d19f74fa994c465cbe4b28e66
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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