Methanesulfonic Acid → Methyl 6-hydroxy-1-naphthoate

HRID 1693641Notes

Reaction equation

HRID 1693641 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): 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-756f2fd274354b1680b2648cb512fe11
Source dataset
uspto-grants-2012_04
Patent number
US08158665B2

Reaction notes

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