Cyclopentadiene → Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl ester

HRID 840999Notes

Reaction equation

HRID 840999 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])C=C.O1CC[CH2:17][CH2:16]1>>[CH:2]12[CH2:1][CH:5]([CH:16]=[CH:17]1)[CH2:4][CH:3]2[C:6]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

4

Reactant 3

HCID 7612CyclopentadieneHCID 8028TetrahydrofuranHCID 15458tert-Butyl acrylate

Product 1

HCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterYield 90.7%

Procedure

In a reactor, cyclopentadiene (66 g) and tetrahydrofuran solvent (500 g) were charged, and the mixture was stirred homogeneously. To the reaction mixture, tert-butyl acrylate (128 g) was added, and the resultant mixture was stirred at a temperature between −30° C. and 60° C. for about 10 hours to carry out the reaction. When the reaction was completed, the solvent was removed by using a rotary evaporator, and the residue was distilled under reduced pressure to obtain 176 g (yield: 90%) of tert-butyl 5-norbornene-2-carboxylate represented by chemical formula VIIa.

Workup

  1. customthe reaction
  2. customthe solvent was removed
  3. customa rotary evaporator
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-7a2dc99243d645668ef537450e4421a2
Source dataset
uspto-grants-2002_04
Patent number
US06369181B1

Reaction notes

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