Iodine → HCID 88744272, compound

HRID 444116Notes

Reaction equation

HRID 444116 reaction equation
[Mg:1].[CH2:2]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][CH3:5].II.[CH2:13]([Cl:17])[CH2:14][CH2:15][CH3:16]>CCCCCCC>[CH2:13]([Cl:17])[CH2:14][CH2:15][CH3:16].[Mg:1].[CH2:2]([O:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 807Iodine3×HCID 8005Butyl Chloride4×HCID 8909Butyl etherHCID 5462224Magnesium

Product 1

HCID 88744272HCID 88744272, compound

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

The preparation was carried out in a one liter, three-necked flask fitted with a tap adaptor, a stirring rod (plus air-tight seal) and a two-necked adaptor holding a gas-balanced dropping funnel and water cooled condenser. Into this flask were placed magnesium turnings (13.2 g, 0.54 mol) and pure, dry, air-free heptane (375 cm3) in which was dissolved n-butyl chloride (3 cm3, 28 mmol). Into the dropping funnel was placed a solution of n-butyl chloride (52.3 cm3, 0.5 mol) dissolved in di-n-butyl ether (83.3 cm3, 0.5 mol). The mixture in the flask was stirred and gently heated to reflux the mixture while a little of the n-butyl chloride solution, plus a few crystals of iodine, were added. The stirring was stopped occasionally and the mixture studied to watch for fading of the deep violet iodine colouration and the formation of bubbles. After 5 to 10 minutes the start of the reaction was signalled by the disappearance of the iodine colouration. Stirring was then resumed and sufficient heat applied to keep the mixture refluxing, while the n-butyl chloride solution was added dropwise over a period of one hour. The reaction mixture was then stirred for a further four hours.

Workup

  1. customfitted with a tap adaptor
  2. customa stirring rod (plus air-tight seal)
  3. customInto this flask were placed
  4. temperaturegently heated
  5. stirringStirring
  6. temperaturesufficient heat
  7. additionwas added dropwise over a period of one hour
  8. stirringThe reaction mixture was then stirred for a further four hours

Sources & evidence

ORD record
ord-1544ef2176f4478fa932ac12694eb81b
Source dataset
uspto-grants-1981_04
Patent number
US04263168

Reaction notes

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