Water → 1,5-Dimethoxynaphthalene

HRID 575493

Reaction equation

HRID 575493 reaction equation
[C:1]1(O)[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([OH:11])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].S(OC)(O[CH3:23])(=O)=O.O>CC(C)=O>[CH3:23][O:11][C:6]1[C:5]2[C:10](=[C:1]([O:16][CH3:13])[CH:2]=[CH:3][CH:4]=2)[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 67491,5-DihydroxynaphthaleneHCID 11430Potassium Carbonate

Product 1

HCID 2525271,5-DimethoxynaphthaleneYield 95.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Naphthalene-1,5-diol (16.0 g, 100 mmol) and potassium carbonate (27.6 g, 200 mmol) were stirred in acetone (300 mL) and dimethyl sulfate (32 mL) was added using syringe. The mixture was then heated to reflux under nitrogen overnight. Water (300 mL) was added after the mixture was cooled to room temperature. The precipitate was collected by filtration and washed with water (4×50 mL), then methanol (3×50 mL). After drying under vacuum, the solid was heated at reflux in ethanol (300 mL) for 2 hours. After cooling to room temperature, the desired product was then collected by filtration to give a pale brown solid (17.9 g, 95.2%). 1H NMR (500 MHz, CDCl3): δ 7.45 (d, J=8.5 Hz, 2H), 7.33 (t, J=8.5 Hz, 2H), 6.83 (d, J=8.5 Hz, 2H), 4.00 (s, 6H).

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux under nitrogen overnight
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water (4×50 mL)
  5. customAfter drying under vacuum
  6. temperaturethe solid was heated
  7. temperatureat reflux in ethanol (300 mL) for 2 hours
  8. temperatureAfter cooling to room temperature
  9. filtrationthe desired product was then collected by filtration

Sources & evidence

ORD record
ord-d495cc15923b4cdcbbd5c28f1c784c6f
Source dataset
uspto-grants-2015_05
Patent number
US09035004B2

Linked notes

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