N([O-])=O.[Na+].N[C:6]1[C:15]2[O:14][CH:13]([C:16]([Cl:19])([Cl:18])[Cl:17])[O:12][CH:11]([C:20]([Cl:23])([Cl:22])[Cl:21])[C:10]=2[CH:9]=[C:8]([CH3:24])[CH:7]=1.C(O)C.S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH3:24][C:8]1[CH:7]=[CH:6][C:15]2[O:14][CH:13]([C:16]([Cl:17])([Cl:19])[Cl:18])[O:12][CH:11]([C:20]([Cl:22])([Cl:23])[Cl:21])[C:10]=2[CH:9]=1Solid sodium nitrite (1.34 g.) was added in portions to a boiling suspension of 8-amino-6-methyl-2,4-bis(trichloromethyl)benzo[1,3]dioxin (4.7 g.) in a mixture of absolute ethanol (20 ml.), toluene (5 ml.) and concentrated sulphuric acid (1.34 ml.). The mixture was heated under reflux for 3 hours, cooled to ambient temperature and evaporated to dryness under reduced pressure. The oily residue was triturated with petroleum ether (b.p. 60°-80° C.) and filtered, and the solid was crystallised from aqueous ethanol to give 6-methyl-2,4-bis(trichloromethyl)benzo[1,3]dioxin m.p. 134°-135° C.
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