1,3-Butadiene → Octahydro-1,4-methanonaphthalene

HRID 7269

Reaction equation

HRID 7269 reaction equation
[CH2:1]1[CH:5]2[CH:6]=[CH:7][CH:3]([CH2:4]2)[CH2:2]1.[CH2:8]=[CH:9][CH:10]=[CH2:11]>CC1C=CC(O)=CC=1>[CH:3]12[CH2:4][CH:5]([CH:1]3[C:2]1=[CH:11][CH2:10][CH2:9][CH2:8]3)[CH2:6][CH2:7]2

Participants

4

Reactant 2

HCID 78451,3-ButadieneHCID 103522-Norbornene2×

Product 1

HCID 13446694Octahydro-1,4-methanonaphthaleneYield 145.8%

Reagents, catalysts & solvents 1

HCID 2879P-CresolCatalyst

Conditions

Temperature
200 °C

Procedure

A 400 ml autoclave was charged with bicyclo[2,2,1]-2-heptene (152 g, Aldrich), 4-methylphenol (1 g, Aldrich), and butadiene (110 g). The mixture was heated at 200° C. for 10 hours. The reaction mixtures from four identical reactions were combined and distilled at atmosphere to give starting bicyclo[2,2,1]-2-heptene (307 g). Further distillation at reduced pressure afforded octahydro-1,4-methanonaphthalene (349 g with 97–98% purity, bp 47° C./0.05 Torr, yield 73%, based on consumed bicyclo[2,2,1]-2-heptene) and about 120 g of product with lower purity (bp 47° C./2 Torr to 58° C./0.16 Torr).

Workup

  1. distillationdistilled at atmosphere
  2. customto give
  3. distillationFurther distillation at reduced pressure

Sources & evidence

ORD record
ord-dc825329a9534658b229511a87c5a84d
Source dataset
uspto-grants-2006_08
Patent number
US07084314B1

Linked notes

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