6-Hydroxy-2-naphthoic acid → Methyl 6-hydroxy-2-naphthoate

HRID 1108618Notes

Reaction equation

HRID 1108618 reaction equation
Cl.[CH3:2]O.[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([OH:17])=[O:16])[CH:9]=[CH:8]2>>[OH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([C:15]([O:17][CH3:2])=[O:16])[CH:9]=[CH:8]2

Participants

3

Reactant 2

HCID 855576-Hydroxy-2-naphthoic acidHCID 21893726Hydrochloride methanol

Product 1

HCID 390995Methyl 6-hydroxy-2-naphthoate

Procedure

15 ml of 10% hydrogen chloride-methanol was added to 1.0 g (5.31 mmol) of 6-hydroxy-2-naphthoic acid and the mixture was stirred at room temperature for one day. After the reaction mixture was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, washed twice with water, and dried (MgSO4). The solvent was distilled off to obtain 1.07 g (5.29 mmol) of methyl 6-hydroxy-2-naphthoate as a pale yellowish brown powder. Its spectroscopic data are as follows:

Workup

  1. concentrationAfter the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed twice with water
  4. dry with materialdried (MgSO4)
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-1c7d85439ffd488397360264c70a056f
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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