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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2120519Generated: October 30, 2026

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

https://huagongshe.com/reaction/2120519

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDicyclopentadieneHCID 6492—
Reactanttert-Butyl acrylateHCID 15458—
SolventTolueneHCID 1140—
ProductBicyclo[2.2.1]hept-5-ene-2-carboxylic acid, 1,1-dimethylethyl esterHCID 1560733464.4%

Reaction Steps

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:

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06692887B1
Source datasetuspto-grants-2004_02
ORD IDord-124910d123bd483eb44cd2afcdb38921
Source noteuspto-grants-2004_02