Water → 1-Ethenyl-4-(2-methylpropyl)benzene

HRID 1440488Notes

Reaction equation

HRID 1440488 reaction equation
Cl[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1)[CH3:3].[Na].O>CN(C)C=O>[CH2:10]([C:7]1[CH:6]=[CH:5][C:4]([CH:2]=[CH2:3])=[CH:9][CH:8]=1)[CH:11]([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962Water2×HCID 30173041-(1-Chloroethyl)-4-(2-methylpropyl)benzeneHCID 5360545Sodium

Product 1

HCID 5761461-Ethenyl-4-(2-methylpropyl)benzeneYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flat bottomed vial was charged with a mixture of 1-chloro-1-(4-isobutylphenyl)ethane (500 mg; 2.54 mmol), 250 mg (11 mmol) of sodium spheres in 5 mL of dry dimethylformamide. The vial was immersed in an ultrasound cleaner filled with water, and sonicated at room temperature for 2 hours. The reaction mixture was carefully treated with 30 mL of water and extracted with ether (3×30 mL). The ether extract was washed with water (3 ×15 mL) and dried over anhydrous MgSO4. It was filtered and stripped off the solvent to obtain 382 mg (94% yield) of pure 4-isobutylstyrene.

Workup

  1. customsonicated at room temperature for 2 hours
  2. extractionextracted with ether (3×30 mL)
  3. extractionThe ether extract
  4. washwas washed with water (3 ×15 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationIt was filtered

Sources & evidence

ORD record
ord-80fbbbb7a18a485c896228fd663f9efd
Source dataset
uspto-grants-1996_03
Patent number
US05498800

Reaction notes

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