2-(1-Bromoethyl)-6-methoxynaphthalene → 2-Vinyl-6-methoxynaphthalene

HRID 2254374Notes

Reaction equation

HRID 2254374 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:13](Br)[CH3:14])[CH:9]=2)[CH:4]=1>N1C(C)=CC(C)=CC=1C.C(OCC)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH:13]=[CH2:14])[CH:9]=2)[CH:4]=1

Participants

4

Reactant 1

HCID 102209392-(1-Bromoethyl)-6-methoxynaphthalene

Product 1

HCID 6035352-Vinyl-6-methoxynaphthalene

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 79532,4,6-TrimethylpyridineSolvent

Procedure

The 2-methoxy-6-(1-bromoethyl) naphthalene prepared in Example 9 was dissolved in 8.0 grams of collidine (2,4,6-trimethylpyridine) and the mixture was refluxed for 45 minutes. The product mixture was cooled, diluted with diethylether, and washed with dilute hydrochloric acid. The ether solution was dried over anhydrous magnesium sulfate, filtered and the diethylether removed by evaporation. The structure of the resulting product was verified as 2-methoxy-6-vinylnaphthalene by 1H and 13C nuclear magnetic resonance spectroscopic analysis.

Workup

  1. temperaturethe mixture was refluxed for 45 minutes
  2. temperatureThe product mixture was cooled
  3. washwashed with dilute hydrochloric acid
  4. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe diethylether removed by evaporation

Sources & evidence

ORD record
ord-d92de54fe5dd45a4b37dad4e8ce6b371
Source dataset
uspto-grants-1993_08
Patent number
US05235115

Reaction notes

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