Methanesulfonic Acid → Methyl 6-hydroxy-1-naphthoate

HRID 645998Notes

Reaction equation

HRID 645998 reaction equation
[CH3:1]S(O)(=O)=O.[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([OH:19])=[O:18])=[CH:12][CH:11]=[CH:10]2>CO.C(OCC)(=O)C>[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13]([C:17]([O:19][CH3:1])=[O:18])=[CH:12][CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 54638006-Hydroxy-1-naphthoic acid

Product 1

HCID 11367671Methyl 6-hydroxy-1-naphthoateYield 478.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonic acid (18 mL, 0.28 mol) was added to a stirred solution of 6-hydroxy-1-naphthoic acid (262 g, 1.39 mol) in methanol (1 L) under N2 and the reaction mixture was heated at reflux for 18 h. The reaction mixture was cooled to room temperature and concentrated to give a purple solid. The solid was dissolved in ethyl acetate (1 L), washed with water (3×300 mL), saturated sodium bicarbonate solution (2×300 mL), water (500 mL), brine (300 mL) and then dried over anhydrous sodium sulfate. The resulting solution was filtered and concentrated to give 271 g of the product as a pink solid. 1H NMR (400 MHz, d6-DMSO): δ 9.94 (s, 1H), 8.58 (m, 1H), 7.93 (d, J=8 Hz, 1H), 7.86 (d, J=7.0 Hz, 1H), 7.44 (t, J=8 Hz, 1H), 7.22-7.19 (m, 2H), 3.88 (s, 3H). ESI-LCMS m/z 203 (M+H)+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated
  4. customto give a purple solid
  5. washwashed with water (3×300 mL), saturated sodium bicarbonate solution (2×300 mL), water (500 mL), brine (300 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe resulting solution was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f852ed0e0e1d40ca8dbdebfb5caf7fee
Source dataset
uspto-grants-2010_04
Patent number
US07705028B2

Reaction notes

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