Chloride → HCID 178479005, compound

HRID 1388687Notes

Reaction equation

HRID 1388687 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Mg:12].II.[Cl-:15]>CCOCC>[C:6]1([CH2:5][CH2:4][CH2:3][CH2:2][Mg:12][Cl:15])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 807IodineHCID 78543(4-Chlorobutyl)benzeneHCID 5462224Magnesium

Product 1

HCID 178479005HCID 178479005, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

220 ml. of a solution of (4-chlorobutyl)benzene (1083 g., 6.42 mole) in 1280 ml. of ether is added to a flask containing magnesium (241.6 g., 0.9 mole) in 834 ml. of ether. The mixture is refluxed and a few crystals of iodine are added. The reaction initiates after about 30 minutes. When the initial reaction subsides, the remaining chloride solution is added at a rate sufficient to maintain reflux (addition time about 1.5 hours). Reflux is maintained an additional 2.5 hours and the mixture is cooled and allowed to stir overnight under argon at room temperature to give the Grignard solution, (4-phenylbutyl)magnesium chloride.

Workup

  1. temperatureThe mixture is refluxed
  2. customWhen the initial reaction subsides
  3. temperatureto maintain
  4. temperaturereflux
  5. addition(addition time about 1.5 hours)
  6. temperatureReflux
  7. temperatureis maintained an additional 2.5 hours
  8. temperaturethe mixture is cooled

Sources & evidence

ORD record
ord-33b92cdde38441e480bd27a63948e8a6
Source dataset
uspto-grants-1984_02
Patent number
US04432972

Reaction notes

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