Hydrochloric Acid → 4-Phenyl-1,2-dihydronaphthalene

20.0 mL (20.4 mmol) 1.02 M mesitylmagnesium bromide in THF was added over 10-15 minutes to a solution of 2.66 mL (20.0 mmol) 1-tetralone and 4.56 mL (22.0 mmol) diphenyl chlorophosphate in 4 mL THF at 0° C. The solution was stirred at 0° for 30 min, allowed to warm to room temperature, and then stirred for an additional 30 min. The reaction mixture was then treated with 0.140 g (1 mol%) dichlorobis(triphenylphosphine)palladium and warmed to 65°. 11.5 mL (24.0 mmol) 2.08 M phenylmagnesium chloride in THF was added over 5-10 minutes, resulting in a gentle reflux of the solvent. After stirring at 65° for 30 min, the mixture was cooled to room temperature 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 (25 mL). The combined organic phase was washed sequentially with 3 N HCl (15 mL), 3 N NaOH (twice, with 15 mL each time), and brine (20 mL). The resulting organic phase was dried (MgSO4), concentrated, and then distilled using a Kugelrohr apparatus (oven temp=120-150° C.); 0.1 torr) to provide 3.51 g 1-phenyl-3,4-dihydronaphthalene (85% yield on 1-tetralone).

1. stirringstirred for an additional 30 min
2. temperaturewarmed to 65°
3. customresulting in
4. temperaturea gentle reflux of the solvent
5. stirringAfter stirring at 65° for 30 min
6. temperaturethe mixture was cooled to room temperature
7. customThe phases were separated
8. extractionthe aqueous portion was extracted with pentane (25 mL)
9. washThe combined organic phase was washed sequentially with 3 N HCl (15 mL), 3 N NaOH (twice, with 15 mL each time), and brine (20 mL)
10. dry with materialThe resulting organic phase was dried (MgSO4)
11. concentrationconcentrated
12. distillationdistilled
13. customa Kugelrohr apparatus (oven temp=120-150° C.)

ORD record

ord-e56e2d7b53654526bc3866bcdc34c831

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06608212B1