Iodine → 1,2-Di-p-tolylethane

HRID 841117Notes

Reaction equation

HRID 841117 reaction equation
II.[CH3:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[CH:6][CH:5]=1>C1COCC1>[C:4]1([CH3:3])[CH:11]=[CH:10][C:7]([CH2:8][CH2:3][C:4]2[CH:11]=[CH:10][C:7]([CH3:8])=[CH:6][CH:5]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 807IodineHCID 77224-Methylbenzyl chloride

Product 1

HCID 108541,2-Di-p-tolylethaneYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 9.55 g Mg (0.39 mol) and a crystal of I2 in 500 ml anhydrous THF was added a solution of 100 g p-methylbenzylchloride (0.71 mol) in 150 ml anhydrous THF under an inert atmosphere in 30 minutes. The exothermic reaction caused the mixture to reflux. Subsequently the reaction mixture was refluxed for 3 hours. The solvent was evaporated under reduced pressure and the remaining white solid was treated with 400 ml pentane and 400 ml aqueous 10% HCl. The organic layer was extracted with 150 ml saturated NaCl (2 times) and dried with MgSO4. The solvent was evaporated under reduced pressure giving 69.8 g (0.33 mol, 93%) product as a white powder.

Workup

  1. customThe exothermic reaction
  2. temperatureto reflux
  3. temperatureSubsequently the reaction mixture was refluxed for 3 hours
  4. customThe solvent was evaporated under reduced pressure
  5. additionthe remaining white solid was treated with 400 ml pentane and 400 ml aqueous 10% HCl
  6. extractionThe organic layer was extracted with 150 ml saturated NaCl (2 times)
  7. dry with materialdried with MgSO4
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-990c53805b214b7d847908342f84d733
Source dataset
uspto-grants-2002_04
Patent number
US06369254B1

Reaction notes

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