Hydrochloric Acid → 1-Phenyl-cycloheptene

Temperature

0 °C

Mesitylmagnesium bromide (18.0 mL, 18.0 mmol, 1.0 M in THF) was added over 15 minutes to a solution of cycloheptanone (2.0 g, 17.8 mmol) and diphenyl chlorophosphate (1.1 eq.) in THF (5 mL) at 0° C. The solution was stirred at 0° C. for 30 min, whereafter the solution was allowed to reach room temperature. After stirring the solution for 30 min, dichlorobis(triphenylphosphine)palladium (126 mg, 1 mol %) was added and the solution was warmed to 65° C. Phenylmagnesium chloride (10.8 mL, 1.2 equivalents in THF) was added over 10 minutes, resulting in a gentle reflux of the solvent. After stirring at 65° C. for 30 minutes, the mixture was cooled to rt and poured into a mixture of 3 N HCl (30 mL) and pentane (30 mL). The phases were separated, and the aqueous portion was extracted with pentane (30 mL). The combined organic phase was washed sequentially with 3 N HCl (20 mL), 3 M NaOH (2×20 mL), and brine (20 mL), and dried over MgSO4. Evaporation of the solvent followed by distillation using a Kugelrohr apparatus (oven temperature 100-140° C., 0.065 torr) yielded 1-phenylcycloheptene (1.29 g, 43%).

1. customto reach room temperature
2. stirringAfter stirring the solution for 30 min
3. temperaturethe solution was warmed to 65° C
4. customresulting in
5. temperaturea gentle reflux of the solvent
6. stirringAfter stirring at 65° C. for 30 minutes
7. temperaturethe mixture was cooled to rt
8. customThe phases were separated
9. extractionthe aqueous portion was extracted with pentane (30 mL)
10. washThe combined organic phase was washed sequentially with 3 N HCl (20 mL), 3 M NaOH (2×20 mL), and brine (20 mL)
11. dry with materialdried over MgSO4
12. customEvaporation of the solvent
13. distillationfollowed by distillation
14. customa Kugelrohr apparatus (oven temperature 100-140° C., 0.065 torr)

ORD record

ord-cf55e55e22074901a516bc2628059231

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822548B2