1-Hexene → 5-Butyl-2-Norbornene 1-Hexene

HRID 2163748Notes

Reaction equation

HRID 2163748 reaction equation
[CH2:1]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH:6]1[CH:7]=[CH:8]2)[CH2:2][CH2:3][CH3:4].[CH2:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH3:17].[I-].C([Al+]CC)C>C1(C)C=CC=CC=1>[CH2:1]([CH:5]1[CH2:10][CH:9]2[CH2:11][CH:6]1[CH:7]=[CH:8]2)[CH2:2][CH2:3][CH3:4].[CH2:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 115971-HexeneHCID 168020Bicyclo[2.2.1]hept-2-ene, 5-butyl-HCID 16686130AlEt2I

Product 1

HCID 867362595-Butyl-2-Norbornene 1-Hexene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 ml dry toluene cosolvent, 7 ml 5-butyl-2-norbornene, 0.5 ml 1-hexene solution, and 0.6 ml diethylaluminum iodide solution were charged to a dry, nitrogen-purged 7 oz. bottle. 0.75 ml of the MoCl5 solution was charged last with shaking. After 0.5 hour the reaction was shortstopped using a mixture of 0.1 ml ethanolamine, 0.5 ml Solution A and 1 ml of an antioxidant solution (0.1 g/ml of 2,2'-methylenebis-[4-methyl-6-t-butylphenol] in toluene). The polymer cement was coagulated using excess Solution A in a Waring blender. A solid weighing 6.4 grams was recovered after being filtered and vacuum dried at 60° C. It was found to be a ring-opened 5-butyl-2-norbornene/1-hexene copolymer having a DSV of about 0.88.

Workup

  1. custompurged 7 oz. bottle
  2. addition0.75 ml of the MoCl5 solution was charged last
  3. additiona mixture of 0.1 ml ethanolamine, 0.5 ml Solution A and 1 ml of an antioxidant solution (0.1 g/ml of 2,2'-methylenebis-[4-methyl-6-t-butylphenol] in toluene)
  4. customwas recovered
  5. filtrationafter being filtered
  6. customvacuum dried at 60° C

Sources & evidence

ORD record
ord-395de71f02a54b3587b6d875641eb5aa
Source dataset
uspto-grants-1979_01
Patent number
US04136247

Reaction notes

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