Water → 2,7-Dimethoxynaphthalene

HRID 428152

Reaction equation

HRID 428152 reaction equation
O[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[CH:3]=1.S([O:18][CH3:19])(OC)(=O)=O.[C:20](=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH3:20][O:12][C:6]1[CH:7]=[CH:8][C:9]2[C:4](=[CH:3][C:2]([O:18][CH3:19])=[CH:11][CH:10]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 113972,7-NaphthalenediolHCID 11430Potassium Carbonate

Product 1

HCID 770212,7-Dimethoxynaphthalene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methylation of 2,7-dihydroxynaphthalene (10 g:62.43 mmol) is carried out in acetone (100 ml) in the presence of dimethyl sulphate (12.06 ml:127 mmol:2.03 eq.) and dry potassium carbon-ate (42.3 g:306 mmol:4.9 eq.). The temperature of the reaction medium is 56° C. for 6 hours and then 40° C. for 12 hours. Hydrolysis (7.4 ml of water) requires 2 hours of stirring at ambient temperature. After filtering off the salts over Celite and concentrating the remaining filtrate, extraction with dichloromethane yields an organic phase, which, after evaporation, has the appearance of a beige solid. The latter is rendered colourless using active carbon and then recrystallised from a PE/CH2Cl2 mixture.

Workup

  1. wait40° C. for 12 hours
  2. waitrequires 2 hours
  3. filtrationAfter filtering off the salts over Celite
  4. concentrationconcentrating
  5. extractionthe remaining filtrate, extraction with dichloromethane
  6. customyields an organic phase, which
  7. customafter evaporation
  8. customrecrystallised from a PE/CH2Cl2 mixture

Sources & evidence

ORD record
ord-b43353e91a1e44ef95ab27b702fc51a0
Source dataset
uspto-grants-2001_11
Patent number
US06313160B1

Linked notes

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