CC1C=C(C)C=C(C)C=1O.[H-].[Na+].[Cl:13][C:14]1[C:19](C)=[C:18]([Cl:21])[CH:17]=[C:16]([CH3:22])[N+:15]=1[O-:23]>C1COCC1>[Cl:13][C:14]1[CH:19]=[C:18]([Cl:21])[CH:17]=[C:16]([CH3:22])[N+:15]=1[O-:23]To a solution of 2,4,6-trimethylphenol (415 mg, 3.05 mmol) in dry THF (20 ml) was treated with 60% sodium hydride in oil (122 mg, 3.05 mmol) at room temperature. After all H2 was evolved, 2,4-dichloro-3,6-dimethyl-pyridine 1-oxide (585.4 mg, 3.05 mmol) was added and the resulting mixture was heated at reflux for 2 hours. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was dried and concentrated to dryness to give solid. The solid was recrystallized from pet ether to give 802 mg (90%) of the title compound as white crystals. mp 106107° C. 1H NMR (CDCl3) δ 7.04 (s, 1H), 6.78 (s, 2H), 2.41 (s. 3H). 2.36 (s, 3H), 2.22 (s. 3H), 2.06 (s, 6H) ppm.
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