Water → Methyl 3-Methoxy-2-naphthoate

HRID 1457933Notes

Reaction equation

HRID 1457933 reaction equation
[OH:1][C:2]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.S([O:20][CH3:21])(OC)(=O)=O.[C:22]([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[CH3:22][O:1][C:2]1[C:11]([C:12]([O:20][CH3:21])=[O:14])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 71043-Hydroxy-2-naphthoic acidHCID 11430Potassium Carbonate

Product 1

HCID 296952Methyl 3-Methoxy-2-naphthoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Hydroxy-3-naphthoic acid (18.8 g; 100 mmol), dimethyl sulfate (1 eq.) and anhydrous K2CO3 (4.8 eq.) in 500 cm3 of anhydrous acetone are maintained at reflux for 6 h. 25 cm3 of water are added to the cooled mixture, which is stirred at room temperaure for 2 h. After filtration, ether is added and the solution is dried over MgSO4. The solvent is evaporated off to give the compound, which is purified by flash chromatography on silica gel (eluent: ether/petroleum ether). Oil.

Workup

  1. temperatureat reflux for 6 h
  2. filtrationAfter filtration, ether
  3. additionis added
  4. dry with materialthe solution is dried over MgSO4
  5. customThe solvent is evaporated off
  6. customto give the compound, which
  7. customis purified by flash chromatography on silica gel (eluent: ether/petroleum ether)

Sources & evidence

ORD record
ord-6af9b4b333e44fef838fe0be9a709ef2
Source dataset
uspto-grants-1998_12
Patent number
US05849781

Reaction notes

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