Methanol → Methyl 6-hydroxy-2-naphthoate

HRID 969474Notes

Reaction equation

HRID 969474 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>S(=O)(=O)(O)O>[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-naphthoateYield 84%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 15.7 g (83.4 mmol) of 6-hydroxy-2-naphthoic acid is refluxed for 8 hours in a mixture of 160 ml of methanol and 8 ml of concentrated sulfuric acid. After cooling, the product precipitates out. After filtration and washing with isopropyl ether, 14.1 g of methyl 6-hydroxynaphthalene-2-carboxylate are obtained in the form of a beige-colored solid in a yield of 84%.

Workup

  1. temperatureAfter cooling
  2. customthe product precipitates out
  3. filtrationAfter filtration
  4. washwashing with isopropyl ether, 14.1 g of methyl 6-hydroxynaphthalene-2-carboxylate
  5. customare obtained in the form of a beige-colored solid in a yield of 84%

Sources & evidence

ORD record
ord-254080d33fd046a49aa7764d1420b975
Source dataset
uspto-grants-2007_12
Patent number
US07307078B2

Reaction notes

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