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

Participants

Reaction Steps

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).

Provenance & Evidence