Dimethyl Sulfate → 1,3-Dimethoxynaphthalene

HRID 324936Notes

Reaction equation

HRID 324936 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4](O)[CH:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].S(OC)(O[CH3:23])(=O)=O.[OH-].[Na+]>CC(C)=O>[CH3:23][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([O:16][CH3:13])[CH:3]=1

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 86011,3-DihydroxynaphthaleneHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 8707561,3-DimethoxynaphthaleneYield 85.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 1,3-Dihydroxynaphthalene (15 g, 93.6 mmol) and potassium carbonate (20 g, 144.7 mmol) in acetone (200 ml) was added dimethyl sulfate (21 ml, 222 mmol). After stirring over-night the reaction mixture was mixed with 10% sodium hydroxide (100 ml) and extracted with ethyl acetate (200 ml×2) The organic layer was washed with water (100 ml×2), evaporated, and the residue stirred with ammonium hydroxide (50 ml) for 2 hrs to quench any unreacted dimethyl sulfate. Product was extracted with ethyl acetate (200 ml) and was washed with water (100 ml×2) and brine (100 ml). The solvent was evaporated yielding 15 g (85%) of 6.

Workup

  1. extractionextracted with ethyl acetate (200 ml×2) The organic layer
  2. washwas washed with water (100 ml×2)
  3. customevaporated
  4. stirringthe residue stirred with ammonium hydroxide (50 ml) for 2 hrs
  5. customto quench any unreacted dimethyl sulfate
  6. extractionProduct was extracted with ethyl acetate (200 ml)
  7. washwas washed with water (100 ml×2) and brine (100 ml)
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c558d20c843d46cbbd1cbaf15986d205
Source dataset
uspto-grants-2001_04
Patent number
US06221604B1

Reaction notes

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