Benzyl Alcohol → Allyl benzyl ether

In 870 g of tetrahydrofuran were dissolved 218 g (2 mol) of benzyl alcohol 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 potassium t-butoxide 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 299 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 299 g of a crude end product
12. customthe subsequent reaction
13. customwithout further purification

ORD record

ord-9912215b60b643f1bbc633528a9d9ab1

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06682869B2