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Sodium Hydroxide → 1-(2,6-Dimethoxyphenyl)naphthalene

HRID 54027
Notes
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Reaction equation

HRID 54027 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:10][CH3:11].[C:12]1(OB(O)O)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:20]1([C:2]2[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=2[O:10][CH3:11])[C:21]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[CH:18][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 6122962-Bromo-1,3-dimethoxybenzeneHCID 13862914Naphthylboric acid

Product 1

HCID 154981511-(2,6-Dimethoxyphenyl)naphthaleneYield 78.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 31275
1,4-Dioxane
Solvent

Procedure

To a solution of 1-bromo-2,6-dimethoxybenzene, (2.63 g, 12.1 mmol), tetrakis(triphenylphosphine)palladium (0) (0.91 g, 0.76 mol) and 1-naphthylboric acid (4.16 g, 23.9 mmol) in 1,4-dioxane (160 ml), a 2N aqueous solution of sodium hydroxide (13 ml) was added, and the mixture was heated to reflux. After cooling, the solvent was evaporated off, and the residue was dissolved in diethyl ether. The diethyl ether solution was washed with water and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated off, and the residue was purified by silica gel column chromatography (developing phase: n-hexane/ethyl acetate=5/1) to obtain 1-naphthyl-2,6-dimethoxybenzene (2.50 g).

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureAfter cooling
  3. customthe solvent was evaporated off
  4. dissolutionthe residue was dissolved in diethyl ether
  5. washThe diethyl ether solution was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThen, the solvent was evaporated off
  8. customthe residue was purified by silica gel column chromatography (developing phase: n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-0aae8bddb0dc42ebbc926bf057bf5887
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05621129

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes