Tetrahydrofuran → Benzophenone

Temperature

25 °C

To an ice-cooled solution of 1-(3-cyanobenzyl)-4-(2-methoxyphenyl)piperazine (16.5 g, 53.7 mmol) in 800 mL of tetrahydrofuran was added a solution of phenylmagnesium bromide in ethyl ether (53.6 mL, 3.0M) under nitrogen. The solution was slowly warmed to 25° C. and then brought to reflux. After 8 h of reflux, the reaction mixture was subsequently cooled to 0° C., and ice cold 6N HCl solution (650 mL) was added. The reaction mixture was then stirred at ambient temperature for 8 h. After cooling, the reaction mixture was poured into a separatory funnel and washed with ether. The aqueous layer was then basified with K2CO3 and then extracted with chloroform. The organic extracts were combined, dried (Na2SO4), and concentrated to provide a dark brown oil. This material was purified on a Waters Delta Prep 3000 LC apparatus (10% hexaneschloroform) to afford 19.4 g (93%) of desired benzophenone as a brown oil whose 1H NMR in CDCl3 was consistent with the desired structure.

1. temperatureto reflux
2. temperatureAfter 8 h of reflux
3. temperaturethe reaction mixture was subsequently cooled to 0° C.
4. temperatureAfter cooling
5. additionthe reaction mixture was poured into a separatory funnel
6. washwashed with ether
7. extractionextracted with chloroform
8. dry with materialdried (Na2SO4)
9. concentrationconcentrated
10. customto provide a dark brown oil
11. customThis material was purified on a Waters Delta Prep 3000 LC apparatus (10% hexaneschloroform)

ORD record

ord-b8fdc71907cc4b6e81329b00639ae127

Source dataset

uspto-grants-1994_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05332743