Carbon Dioxide → 2-adamantyl Chloroformate

15.2 g (0.10 mole) of 2-adamantanol and 12.1 g (0.10 mole) of N,N-dimethylaniline were dissolved in 200 ml of dry ether and added to 105 ml (0.20 mole) of phosgene in toluene (20%) over a period of 1 hour. The reaction flask was kept at 0° C. and was equipped with a stirrer and a dry ice condensor. The product was stirred at room temperature for another hour, after which the solution was cooled on ice and 10 ml of ice cold water was added carefully. The water and the toluene phases were quickly separated and the toluene was quickly washed with 50 ml of 0.5N HCl, 50 ml of 0.5N NaOH and 50 ml of H2O. The toluene solution was dried over magnesium sulfate and evaporated in vacuo. The residue was dissolved in dry n-hexane and filtered. The hexane was evaporated and the residue was distilled in vacuo to give 2-adamantanyl chloroformate bp15 135° C., nD19 1.521, IR (CO) 1770 cm-1.

1. customwas kept at 0° C.
2. customwas equipped with a stirrer
3. additionwas added carefully
4. customThe water and the toluene phases were quickly separated
5. washthe toluene was quickly washed with 50 ml of 0.5N HCl, 50 ml of 0.5N NaOH and 50 ml of H2O
6. dry with materialThe toluene solution was dried over magnesium sulfate
7. customevaporated in vacuo
8. dissolutionThe residue was dissolved in dry n-hexane
9. filtrationfiltered
10. customThe hexane was evaporated
11. distillationthe residue was distilled in vacuo

ORD record

ord-1f424b0f8a874e8aa506c8503610969a

Source dataset

uspto-grants-1986_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04591583