N(OC(C)(C)C)=O.N[C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16](=[O:18])[CH3:17])=[C:11]([CH3:19])[CH:10]=1.[ClH:20]>C(#N)C.[Cu](Cl)Cl>[Cl:20][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16](=[O:18])[CH3:17])=[C:11]([CH3:19])[CH:10]=1Anhydrous copper(II) chloride (98.9 g, 0.74 mol) was mixed with tert-butyl nitrite (94.8 g, 0.83 mol) in acetonitrile (1.02 L). The solution was cooled to 0° C. and slowly added with 1-(4-amino-2,6-dimethylphenyl)ethanone (100 g, 0.61 mol) in a period of 5.0 min. After the addition was completed, the reaction mixture was warmed to room temperature, and was poured into an aqueous hydrochloric acid solution (20%, 1.0 L). The solution was extracted with EtOAc (800 mL), and the organic layer was separated, washed with H2O (1.0 L), dried over MgSO4 (s), and concentrated under reduced pressure. The liquid was distilled to give 1-(4-chloro-2,6-dimethylphenyl)ethanone (85.0 g) as yellow oil in 76% yield: 1H NMR (500 MHz, CDCl3) δ 7.02 (s, 2H), 2.45 (s, 3H), 2.22 (s, 6H).
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