Pyridine → 6,6-Dimethylbicyclo[3.1.1]hept-2-ene 2-ethyl chloroformate

Participants

Reaction Steps

16.6 G. (0.1 mole) of 6,6-dimethylbicyclo-[3.1.1]hept-2-ene-2-ethanol and 7.9 g. (8.1 ml., 0.1 mole) of pyridine are thoroughly mixed and added dropwise at 10° C to 125 ml. (0.2 moles) of 17.2% phosgene and benzene over a period of 20 minutes. A white precipitate of pyridine hydrochloride forms immediately. The reaction mixture is stirred in the cold for one hour and at room temperature overnight. A stream of nitrogen is passed through the mixture to remove the excess phosgene and the solution is filtered. The filtrate is evaporated to dryness in vacuo affording 23.4 g. (quantitative yield) of 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethyl chloroformate which infrared analysis indicates to be pure material.

Provenance & Evidence