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ChemicalBook CAS DataBase List 1-(2,5-diMethoxyphenyl)-2-(3-Methoxyphenyl)ethanone
1097016-89-1

1-(2,5-diMethoxyphenyl)-2-(3-Methoxyphenyl)ethanone synthesis

5synthesis methods
-

Yield:1097016-89-1 500 g

Reaction Conditions:

with aluminum (III) chloride in dichloromethane at 0; for 1 h;

Steps:

31.2 Step 2: l-(2,5-Dimethoxyphenyl)-2- -methoxyphenyl)ethanone

1,4-Dimethoxybenzene (400 g, 3.19 mol) was added to a suspension of AICI3 (400 g, 3.5 mol) and dry dichloromethane (10 L) in an ice/dry ice bath. A solution of 2-(3- methoxyphenyl)acetyl chloride (606 g, 3.19 mol) in dichloromethane (1 L) was added dropwise over 3 h keeping the internal temperature below 0 °C. The resulting mixture was stirred at 0 °C for 1 h, poured into ice water (5 L) over 30 min with stirring (exothermic), and then extracted with dichloromethane (5 L x 2). The combined organic layers were washed with 1 Ν aqueous HC1 (2 L), saturated aqueous NaHC03 (2 L), and then brine (2 L). The resulting solution was dried (MgSC>4), concentrated, and purified by silica gel chromatography [petroleum ether (bp: 60-90 °C)/EtOAc-5: l] to give l-(2,5-dimethoxyphenyl)-2-(3-methoxyphenyl)ethanone (500 g). 'H NM (DMSO-de, 300 MHz): δ 7.19 (dd, 1H), 7.05-7.10 (m, 3H), 6.74-6.79 (m, 3H), 4.22 (s, 2H), 3.85 (s, 3H), 3.71 (s, 6H).

References:

WO2014/205136,2014,A1 Location in patent:Paragraph 00439