Hydrochloric Acid → 3-Phenyl-1,2-dihydronaphthalene

Participants

Reaction Steps

1.32 mL (10.0 mmol) 2-tetralone in 5 mL of THF was added to a solution of 5.77 mL (12.0 mmol) 2.08 M phenylmagnesium chloride in THF at 0° C. The mixture was allowed to warm to room temperature, and was then stirred for an additional 1 hour. Tridecane (1.22 mL; 5.00 mmol; internal GC standard) was added, the mixture was cooled to 0°, 10 mL of 6N HCl was added. The mixture was heated to 65° and vigorously stirred for 4 hours. The mixture was then cooled to room temperature and diluted with toluene. GC analysis of the organic phase showed the presence of 2.9 mmol 2-phenyl-3,4-dihydronaphthalene (29% yield on 2-tetralone) and 4.6 mmol 2-tetralone (46% recovery). No benzylic alcohol intermediate from addition of the arylmagnesium reagent to the ketone was detected, indicating that its dehydration to the vinylaromatic had been completed by the warm acid treatment.

Provenance & Evidence