Sodium Hydroxide → 2-Bromo-6-(methoxymethoxy)naphthalene

HRID 1840327Notes

Reaction equation

HRID 1840327 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([OH:14])[CH:8]=[CH:7]2.Br[CH2:16][O:17][CH3:18].[OH-].[Na+]>CN(C)C=O>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH2:16][O:17][CH3:18])[CH:10]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 271446-Bromo-2-naphthalenolHCID 83093Bromomethyl methyl ether

Product 1

HCID 144991972-Bromo-6-(methoxymethoxy)naphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 4.5 g, 112 mmol) was added in small portions to a mixture of 6-bromo-2-naphthol (25.0 g, 112 mmol), bromomethylmethylether (21.0 g, 168 mmol) and dimethylformamide (150 ml). The mixture was stirred at room temperature for 1 h. Sodium hydroxide (200 ml, 1 M) was added and the mixture was extracted with diethyl ether. The product was purified chromatographically, using dichloromethane as solvent. Yield 15.7 g, 52%. Mp 46.8-49.2° C.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. customThe product was purified chromatographically

Sources & evidence

ORD record
ord-47b37f2ff6ee420ea736ab4a6a2bc7e4
Source dataset
uspto-grants-2004_01
Patent number
US06680328B2

Reaction notes

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