Sodium Chloride → 1-Methoxy-4-(1-methylethenyl)benzene

HRID 485932Notes

Reaction equation

HRID 485932 reaction equation
[OH-].[Na+].[Cl-].[Na+].[C:5]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)([CH3:7])=[CH2:6].[CH3:15]I>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[C:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:7])=[CH2:6]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 584247p-Isopropenylphenol

Product 1

HCID 2594141-Methoxy-4-(1-methylethenyl)benzeneYield 45%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A two-liter reaction flask was charged with 375 mls of water, 18.25 gms of sodium hydroxide, 125 mls of saturated sodium chloride, 50 gms of para-isopropenylphenol, 450 cc of methylene chloride, 7.5 gms of tetrabutylammoniumbromide, and 35 mls of methyl iodide. The reaction flask was flushed with nitrogen, and the mixture was stirred overnight. The phases were separated, and the aqueous phase was washed with methylene chloride. The combined organic layers were washed with 5% sodium hydroxide and saturated sodium chloride. The solution was dried over sodium sulfate. The methylene chloride was removed by distillation, and 400 mls of diethyl ether was added to precipitate the phase transfer catalyst. After filtration, the ether was stripped and the residue was distilled to give 25 gms of para-isopropenylanisole for a yield of 45%.

Workup

  1. customA two-liter reaction flask
  2. customThe reaction flask was flushed with nitrogen
  3. customThe phases were separated
  4. washthe aqueous phase was washed with methylene chloride
  5. washThe combined organic layers were washed with 5% sodium hydroxide and saturated sodium chloride
  6. dry with materialThe solution was dried over sodium sulfate
  7. customThe methylene chloride was removed by distillation, and 400 mls of diethyl ether
  8. additionwas added
  9. customto precipitate the phase transfer catalyst
  10. filtrationAfter filtration
  11. distillationthe residue was distilled

Sources & evidence

ORD record
ord-a4febbbf4f57405daf43b950fbd18cab
Source dataset
uspto-grants-1985_08
Patent number
US04538002

Reaction notes

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