Dimethyl Sulfate → 2-Naphthalenol, 3-methoxy-

HRID 1070675Notes

Reaction equation

HRID 1070675 reaction equation
[CH3:1]OS(OC)(=O)=O.[OH:8][C:9]1[C:18]([OH:19])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1.[OH-].[Na+]>O>[CH3:1][O:8][C:9]1[C:18]([OH:19])=[CH:17][C:16]2[C:11]([CH:10]=1)=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 70912,3-DihydroxynaphthaleneHCID 14798Sodium Hydroxide

Product 1

HCID 5999432-Naphthalenol, 3-methoxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylsulfate (32 ml) was added to the solution of 2,3-dihydroxynaphthalene (32 g) and sodium hydroxide (10 M, 32 ml) in water (300 ml). After being stirred for six hours at room temperature, the side product 2,3-dimethoxynaphthalene was filtered off (yield 16.6 g). The water phase was acidified, stirred on ice bath, filtered, washed with water and recrystallized from ethanol-water (3:2). Yield: 13.5 g, melting point 108-109° C.

Workup

  1. filtrationthe side product 2,3-dimethoxynaphthalene was filtered off (yield 16.6 g)
  2. stirringstirred on ice bath
  3. filtrationfiltered
  4. washwashed with water
  5. customrecrystallized from ethanol-water (3:2)

Sources & evidence

ORD record
ord-456579975351486f86a38e998a079427
Source dataset
uspto-grants-2005_06
Patent number
US06903114B2

Reaction notes

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