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

HRID 2120519Notes

Reaction equation

HRID 2120519 reaction equation
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].[CH2:10]1[CH:14]2[CH:15]3C=CC([CH:13]2C=[CH:11]1)C3>C1(C)C=CC=CC=1>[C:6]([O:5][C:1]([CH:2]1[CH2:13][CH:14]2[CH2:15][CH:3]1[CH:11]=[CH:10]2)=[O:4])([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 6492DicyclopentadieneHCID 15458tert-Butyl acrylate

Product 1

HCID 15607334Bicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterYield 64.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into an autoclave with an internal volume of 2 liters, 256.3 g of t-butyl acrylate, 264.4 g of dicyclopentadiene and 1,040 g of toluene were charged, and the reaction was carried out at a temperature of 170° C. or higher for 5 hours. Subsequently, the reaction product was drawn out, and the toluene was evaporated, followed by distillation using a distillation column at 8.0 Torr and 87° C. to obtain 250 g of 5-t-butoxycarbonylbicyclo[2.2.1]hept-2-ene with a purity of 99.9% by weight. Using the same distillation column, the product was distilled at 0.07 Torr and 97 to 102° C. to obtain 100 g of 8-t-butoxycarbonyltetracyclo[4.4.0.12,5.17,10]dodec-3-ene with a purity of 99.9% by weight:

Workup

  1. customthe toluene was evaporated
  2. distillationfollowed by distillation
  3. distillationa distillation column at 8.0 Torr and 87° C.

Sources & evidence

ORD record
ord-124910d123bd483eb44cd2afcdb38921
Source dataset
uspto-grants-2004_02
Patent number
US06692887B1

Reaction notes

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