Dimethyl Sulfate → Methyl 1-methoxy-4-bromo-2-naphthoate

HRID 2042917Notes

Reaction equation

HRID 2042917 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([OH:15])=O)[CH:3]=1.S([O:21][CH3:22])(OC)(=O)=O.[C:23]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:23])=[C:4]([C:13]([O:21][CH3:22])=[O:15])[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2893934-Bromo-1-hydroxynaphthalene-2-carboxylic acid

Product 1

HCID 12084039Methyl 1-methoxy-4-bromo-2-naphthoateYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of hydroxynaphthoic acid 18 (24.7 g, 92.2 mmol), dimethyl sulfate (21.8 mL, 231 mmol), and K2CO3 (31.9 g, 231 mmol) in acetone (200 mL) was refluxed overnight. The solid was filtered, and the filtrate was condensed to give a solid residue, which was recrystallized from EtOAc/hexanes to afford the titled compound 19 (21.2 g, 78%) as a white solid.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationThe solid was filtered
  3. customcondensed
  4. customto give a solid residue, which
  5. customwas recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-14f1c66a7fa84fc399c8bf9f91c1c493
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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