Dimethyl Sulfate → Methyl 1-methoxy-2-naphthoate

HRID 1790293Notes

Reaction equation

HRID 1790293 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.[C:15](=O)([O-])[O-].[K+].[K+].S([O:26][CH3:27])(OC)(=O)=O>CC(C)=O.C(OCC)(=O)C>[CH3:15][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([O:26][CH3:27])=[O:14]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 68441-Hydroxy-2-naphthoic acidHCID 11430Potassium Carbonate

Product 1

HCID 4640332Methyl 1-methoxy-2-naphthoateYield 90.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-hydroxy-naphthalene-2-carboxylic acid (5 g, 26.6 mmol) in acetone (100 mL) was added potassium carbonate (11 g, 79.72 mmol) followed by dimethyl sulfate (7.38 g, 58.46 mmol). The reaction mixture was refluxed overnight and then diluted with ethyl acetate (200 mL) and washed with water. The organic layer was dried (MgSO4), and the solvent was removed to give an oil (5.2 g): 1H NMR (CDCl3) δ 3.98 (s, 3H, CH3), 4.06 (s, 3H, CH3), 7.59 (m, 3H, Ar—H), 7.85 (m, 2H, Ar—H), 8.25 (m, 1H, Ar—H); MS 217 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. washwashed with water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-4d9520f5a9c04390ae86ba1ae95e1a5f
Source dataset
uspto-grants-2006_07
Patent number
US07071225B2

Reaction notes

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