Methanol → Methyl 6-hydroxy-2-naphthoate

HRID 964929Notes

Reaction equation

HRID 964929 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.[CH3:15]O>Cl>[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 887MethanolHCID 855576-Hydroxy-2-naphthoic acid

Product 1

HCID 390995Methyl 6-hydroxy-2-naphthoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

To 6-hydroxy-2-naphthoic acid (Lancaster®) was added methanol and several drops of concentrated HCl. This mixture was refluxed overnight, the solvent was evaporated, and the residue was dissolved in methylene chloride. The resulting solution was washed with saturated NaHCO3 solution, dried over sodium sulfate and evaporated to give crude methyl 6-hydroxy-2-naphthoate of sufficient purity for the next step.

Workup

  1. temperatureThis mixture was refluxed overnight
  2. customthe solvent was evaporated
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washThe resulting solution was washed with saturated NaHCO3 solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-35e2a57388b64d2d905c90aee5e22d0e
Source dataset
uspto-grants-1998_06
Patent number
US05773421

Reaction notes

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