Methyl Bromide → 2-Bromo-6-ethoxynaphthalene

HRID 399359

Reaction equation

HRID 399359 reaction equation
Br[CH3:2].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9](O)[CH:8]=[CH:7]2.[C:15](=[O:18])([O-])[O-].[K+].[K+]>CC(C)=O>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH2:15][CH3:2])[CH:10]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 6323Methyl BromideHCID 11430Potassium CarbonateHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 2368582-Bromo-6-ethoxynaphthalene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

This experimental procedure is an O-alkylation. A solution of bromomethane (48.90 g, 0.45 mol) is added dropwise to a stirred refluxing mixture of 6-Bromo-2-naphthol (40.00 g, 0.18 mol) and potassium carbonate (63.00 g, 0.46 mol) in acetone. The stirred mixture is heated under reflux for 24 hours (ie until glc analysis reveals a complete reaction). The potassium carbonate is filtered off, water is added to filtrate and the product is recrystallised from ethanol to give a yield of 43.92 g (97%).

Workup

  1. temperaturerefluxing
  2. temperatureThe stirred mixture is heated
  3. temperatureunder reflux for 24 hours (ie until glc analysis
  4. customa complete reaction)
  5. filtrationThe potassium carbonate is filtered off
  6. additionwater is added to filtrate
  7. customthe product is recrystallised from ethanol
  8. customto give a yield of 43.92 g (97%)

Sources & evidence

ORD record
ord-a2e80eb80d1047d1a23f28aea9355410
Source dataset
uspto-grants-1998_10
Patent number
US05820781

Linked notes

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