Cyclopentadiene → 5-Norbornene-2-carboxylic acid

HRID 258336

Reaction equation

HRID 258336 reaction equation
[C:1]([O:5]CC#C)(=[O:4])[CH:2]=[CH2:3].[CH:9]1[CH2:13][CH:12]=[CH:11][CH:10]=1.C[SiH](C)Cl>>[CH:11]12[CH2:12][CH:13]([CH:9]=[CH:10]1)[CH2:3][CH:2]2[C:1]([OH:5])=[O:4]

Participants

4

Reactant 3

HCID 7612CyclopentadieneHCID 66108ChlorodimethylsilaneHCID 82655Propargyl acrylate

Product 1

HCID 789495-Norbornene-2-carboxylic acid

Conditions

Temperature
70 °C

Procedure

The propargyl ester of 2-norborn-5-ene carboxylic acid was prepared by Diels-Alder reaction of propargyl acrylate and cyclopentadiene at ambient temperature. Dimethylchlorosilane (56.4g) was added portionwise to 100 grams of this norbornene carboxylate ester and 0.16 g Karstedt catalyst under nitrogen at 70° C. After exotherming to 80° C., the mixture was stirred for 3 hours at 70° C., stripped under light vacuum and then distilled. The product, ##STR13## (84% purity by GC), distilled at 100°-105° C. at 0.07 mm.

Workup

  1. customAfter exotherming to 80° C.
  2. distillationdistilled
  3. distillationThe product, ##STR13## (84% purity by GC), distilled at 100°-105° C. at 0.07 mm

Sources & evidence

ORD record
ord-d85f129d3e2a461f99de5519ad3c12e9
Source dataset
uspto-grants-1993_11
Patent number
US05266670

Linked notes

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