Water → allyl cyclohexyl ether

In 870 g of tetrahydrofuran were dissolved 200 g (2 mol) of cyclohexanol and 224 g (2 mol) of potassium t-butoxide. With stirring at room temperature, 242 g (2 mol) of allyl bromide was added dropwise so that the temperature might not exceed 60° C. At the end of addition, the solution was heated at 60° C. on an oil bath and ripened for one hour at the temperature. The solution was allowed to cool down to room temperature, and 11.2 g (0.1 mol) of t-butoxypotassium was added. With stirring at room temperature, 12.1 g (0.1 mol) of allyl bromide was added dropwise. The solution was heated at 60° C. on an oil bath and ripened for one hour at the temperature. The solution was cooled in an ice bath, and 550 g of water was added. The organic layer was collected. The solvent was distilled off in vacuum, yielding 280 g of a crude end product. The product was used in the subsequent reaction without further purification.

1. customexceed 60° C
2. additionAt the end of addition
3. temperaturethe solution was heated at 60° C. on an oil bath
4. temperatureto cool down to room temperature
5. stirringWith stirring at room temperature
6. temperatureThe solution was heated at 60° C. on an oil bath
7. waitripened for one hour at the temperature
8. temperatureThe solution was cooled in an ice bath
9. customThe organic layer was collected
10. distillationThe solvent was distilled off in vacuum
11. customyielding 280 g of a crude end product
12. customThe product was used in the subsequent reaction without further purification

ORD record

ord-2997996873cd43a4aaa98b171d49d6e4

Source dataset

uspto-grants-2005_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06838224B2