Ethyl Acetate → 4-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-nitrobenzene

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Reaction Steps

4-Chloro-3,5-dimethylnitrobenzene (2.12 g), 1.9 g of 3-isopropyl-4-methoxyphenol, and 1.74 g of potassium carbonate are heated 18 hrs at 125° in 25 ml dimethylsulfoxide. The mixture is poured into ethyl acetate and extracted once with water and five times with brine. The ethyl acetate is dried, filtered, and stripped to yield an oil which is chromatographed on silica gel with 97:3 hexane:ethyl acetate to afford 3,5-dimethyl-4-(3'-isopropyl-4'-methoxyphenoxy)-nitrobenzene. NMR (CDCl3): δ1.1 (6H,d), 2.2 (6H,s), 3.3 (1H,m), 3.7 (3H,s) 6.3 (1H,d of d), 6.6 (1H,d), 6.7 (1H,d), 8.0 (2H, s).

Provenance & Evidence