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

HRID 366976Notes

Reaction equation

HRID 366976 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%

Procedure

In a reactor, 66 g of cyclopentadiene was first put and then mixed with 500 g of tetrahydrofuran. To the reactor, 128 g of t-butyl acrylate was added. Thereafter, these reactants were subjected to a reaction at a temperature of -30 to 60° C. for 10 hrs with stirring. After the completion of the reaction, the solvent was vaporized in vacuo by use of a rotary evaporator then vacuum distilled to produce the title compound: yield is 90%.

Workup

  1. customThereafter, these reactants were subjected to a reaction at a temperature of -30 to 60° C. for 10 hrs
  2. customAfter the completion of the reaction
  3. customthe solvent was vaporized in vacuo by use of a rotary evaporator
  4. distillationvacuum distilled

Sources & evidence

ORD record
ord-9ffa7818d52f4487ada61dff5bedddec
Source dataset
uspto-grants-2000_10
Patent number
US06132926

Reaction notes

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