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

HRID 1871189Notes

Reaction equation

HRID 1871189 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].Cl.[CH3:13]O>>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:13])=[O:7])=[CH:4][C:3]=1[OH:11]

Participants

4

Reactant 3

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

Product 1

HCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl esterYield 96%

Procedure

Through a solution of 4-amino-3-hydroxybenzoic acid (75 g, 0.49 mol) in 2.0 L of dry methanol at room temperature was bubbled anhydrous HCl gas until the solution was saturated. The solution was stirred for 48 hours, then concentrated in vacuo. The product was partitioned between EtOAc and saturated aq. NaHCO3 solution, and the organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo to provide the titled compound (79 g, 96% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was partitioned between EtOAc and saturated aq. NaHCO3 solution
  3. washthe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac3bfd22314b4f4993ab3d2ed5107b6b
Source dataset
uspto-grants-2000_08
Patent number
US06103487

Reaction notes

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