Background and overview[1]
(3-ethylphenyl)(phenyl)methanone is an organic intermediate. Tran et al. reported that (3-ethylphenyl)(phenyl)methanone can be synthesized from ethylbenzene and benzene. Acid chloride was prepared.
Preparation[1]
General/Typical Procedure: To a 10-mL pressurized glass tube with a Teflon-coated septum equipped with a magnetic stirrer, add substrate (1 mmol), benzoyl chloride (1 mmol), and triflate Metal salt (0.1 equiv). Seal the tube and place in the CEM microwave oven at this temperature for the appropriate time. The reaction mixture was allowed to cool to room temperature in a MW oven. After cooling, water (15 mL) was added to the mixture, and the product was extracted with ethyl acetate or dichloromethane (3 × 15 mL). The organic layer was decanted, washed with water, aqueous NaHCO3 and brine; and dried over MgSO4. The solvent was then removed on a rotary evaporator and flash chromatography was performed on silica gel (mixture of hexane and ethyl acetate solvent to elute the product). The product-containing fractions were concentrated and dried under vacuum to give pure product. All products are known compounds; purity and identity of all products were confirmed by GC-MS and 1H and 13C NMR spectra. 4-Ethylbenzophenone,1H NMR (500MHz, CDCl3): δ= 7.78 (dd, J = 8.3, 1.3Hz, 2H), 7.76 -7.72 (m, 2H), 7.56 (s, 1H), 7.46 (t, J = 7.6Hz, 2H), 7.30 (d, J = 8.4Hz, 2H), 2.73 (q, J = 7.6Hz, 2H) , 1.28 (t, J = 7.6Hz, 3H). 13CNMR (125MHz, CDCl3): δ= 196.5,149.4,138.0,135.2, 132.1,130.3,130.1,130.0,129.9,128.4,128.2,127.8,28.9 ,15.2. MS (EI, 70eV): m/z (%) = 210 (50, [M+]).
Main reference materials
[1] Tran P H , Hansen P E , Pham T T , et al. Microwave-Assisted Facile and Rapid Friedel–Crafts Benzoylation of Arenes Catalyzed by Bismuth Trifluoromethanesulfonate[J]. Synthetic Communications, 2014, 44(20):2921- 2929.
