1-Hexene → 5-Methyl-2-Norbornene 1-Hexene

HRID 2163746Notes

Reaction equation

HRID 2163746 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]2[CH2:8][CH:3]1[CH:4]=[CH:5]2.[CH2:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14].[I-].C([Al+]CC)C>C1C=CC=CC=1>[CH3:1][CH:2]1[CH2:7][CH:6]2[CH2:8][CH:3]1[CH:4]=[CH:5]2.[CH2:9]=[CH:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 115971-HexeneHCID 101870Bicyclo[2.2.1]hept-2-ene, 5-methyl-HCID 16686130AlEt2I

Product 1

HCID 867362545-Methyl-2-Norbornene 1-Hexene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

500 ml dry benzene cosolvent, 74 ml 5-methyl-2-norbornene, 12 ml of the 1-hexene solution, and 6 ml of the diethylaluminum iodide solution were charged to a dry, nitrogen-purged quart bottle. 7.5 ml of the MoCl5 solution was charged last, and the bottle was shaken. After 80 minutes the reaction was shortstopped using a mixture of 1.5 ml ethanolamine, 10 ml of antioxidant solution (10 grams of 2,2',2"-tris[3(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy] ethyl isocyanurate in 100 ml benzene), and 1.5 ml Solution A. The polymer cement was coagulated using excess Solution A in a Waring blender. A solid weighing 66.0 grams was recovered after being filtered and vacuum dried at 60° C. It was found to be a ring-opened 5-methyl-2-norbornene/1-hexene copolymer having a DSV of about 1.90.

Workup

  1. custompurged quart bottle
  2. addition7.5 ml of the MoCl5 solution was charged last
  3. additiona mixture of 1.5 ml ethanolamine, 10 ml of antioxidant solution (10 grams of 2,2',2"-tris[3(3,5-di-t-butyl-4-hydroxyphenyl)propionyloxy] ethyl isocyanurate in 100 ml benzene), and 1.5 ml Solution A
  4. customwas recovered
  5. filtrationafter being filtered
  6. customvacuum dried at 60° C

Sources & evidence

ORD record
ord-95e9296371b9490b92adcb62952ff9be
Source dataset
uspto-grants-1979_01
Patent number
US04136247

Reaction notes

Loading…