2,6-Di-tert-butylphenol → 2-Vinyl-6-methoxynaphthalene

HRID 613000Notes

Reaction equation

HRID 613000 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[C:14](C1C=CC=C(C(C)(C)C)C=1O)(C)(C)[CH3:15].CC([O-])=O.[Na+]>CN(C)C(=O)C>[CH:14]([C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1)=[CH2:15]

Participants

5

Reactant 3

HCID 314052,6-Di-tert-butylphenolHCID 787862-Bromo-6-methoxynaphthaleneHCID 517045Sodium Acetate

Product 1

HCID 6035352-Vinyl-6-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

23.7 g of 2-bromo-6-methoxynaphthalene (100 mmol) are dissolved in 150 ml of N,N-dimethylacetamide. 1 mg of 2,6-di-tert-butylphenol, 10 g of NaOAc (1.2 eq) and 50 mg of palladacycle are added. The solution is transferred to a V4A stirred autoclave and is stirred at 140° C. under an ethylene pressure of 20 bar until conversion is complete. Time: from 10 to 16 hours

Workup

  1. stirringis stirred at 140° C. under an ethylene pressure of 20 bar until conversion
  2. customfrom 10 to 16 hours

Sources & evidence

ORD record
ord-1da981796dc7428abd9ea77a3cb09521
Source dataset
uspto-grants-1999_12
Patent number
US06005151

Reaction notes

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