Dicyclopentadiene → HCID 131730273, compound

HRID 1943053Notes

Reaction equation

HRID 1943053 reaction equation
[O:1]1[C:7]23[CH2:8][CH:4]([CH2:5][CH:6]2C=C)[CH2:3][CH:2]13.C1[CH:15]2[CH:16]3[CH:20]=[CH:19][CH:18]([CH:14]2C=C1)[CH2:17]3>>[C:16]12([C:2]34[O:1][C:7]53[CH2:8][CH:4]([CH2:3]4)[CH2:5][CH2:6]5)[CH2:17][CH:18]([CH2:19][CH2:20]1)[CH:14]=[CH:15]2

Participants

3

Reactant 2

HCID 6492DicyclopentadieneHCID 23500937HCID 23500937, compound

Product 1

HCID 131730273HCID 131730273, compoundYield 329.6%

Conditions

Temperature
180 °C

Procedure

To a 2-liter stainless steel autoclave reactor was charged 0.99 kg (7.26 mol) 3-epoxy-5-vinyl norbornane and 0.06 kg (0.45 mol) dicyclopentadiene. Stirring was started, and the reactor evacuated of air and padded with 5 psig nitrogen. Heating to 180° C. commenced, and upon achieving 180° C., the reactor was held for 4 hours at this temperature. At the end of this time, the reactor was cooled to ambient temperature and discharged. The major identified components of the charge, as measured by GC area, were: 0.6% dicyclopentadiene, 81.6% 3-epoxy-5-vinyl norbornane, 1.3% epoxyethylepoxy norbornane, 13.6% norbornenyl epoxy norbornane. A total of four reactions were completed and distilled to produce 0.3 kg norbornenyl epoxy norbornane with assay greater than 96% (GC area).

Workup

  1. customthe reactor evacuated of air
  2. customupon achieving 180° C.
  3. temperatureAt the end of this time, the reactor was cooled to ambient temperature
  4. distillationdistilled

Sources & evidence

ORD record
ord-ea6e8732100e41139f9ac5148d11c399
Source dataset
uspto-grants-2013_03
Patent number
US08389752B2

Reaction notes

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