1-Hexene → 5-Ethyl-2-Norbornene 1-Hexene

HRID 2163738Notes

Reaction equation

HRID 2163738 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2)[CH3:2].[CH2:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH3:15].[I-].C([Al+]CC)C>C1(C)C=CC=CC=1>[CH2:1]([CH:3]1[CH2:8][CH:7]2[CH2:9][CH:4]1[CH:5]=[CH:6]2)[CH3:2].[CH2:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 115971-HexeneHCID 85837Bicyclo(2.2.1)hept-2-ene, 5-ethyl-HCID 16686130AlEt2I

Product 1

HCID 867362585-Ethyl-2-Norbornene 1-Hexene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 ml dry toluene cosolvent, 7 ml 5-ethyl-2-norbornene, 0.8 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, and the bottle was shaken. After 1 hour the reaction was shortstopped using a mixture of 0.8 ml ethanolamine, 3 ml Solution A and 25 ml toluene. 2 ml of an antioxidant solution was added (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 5.9 grams was recovered after being filtered and vacuum dried at 60° C. It was found to be a ring-opened 5-ethyl-2-norbornene/1-hexene copolymer with a DSV of about 1.53.

Workup

  1. custompurged 7 oz. bottle
  2. addition0.75 ml of the MoCl5 solution was charged last
  3. additiona mixture of 0.8 ml ethanolamine, 3 ml Solution A and 25 ml toluene
  4. addition2 ml of an antioxidant solution was added (0.1 g/ml of 2,2'-methylenebis[4-methyl-6-t-butylphenol] in toluene)
  5. customwas recovered
  6. filtrationafter being filtered
  7. customvacuum dried at 60° C

Sources & evidence

ORD record
ord-ef4e22ac525f45cebddab40b6d5fc24d
Source dataset
uspto-grants-1979_01
Patent number
US04136248

Reaction notes

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