[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[C:14](Cl)(=[O:16])[CH3:15].[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C1C=CC=CC=1)([O-])=O>[C:14]([C:4]1[CH:3]=[C:2]([F:1])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[CH:5]=1)(=[O:16])[CH3:15]
A solution of 1-fluoro-7-methoxynaphthalene (13 g, 0.074 mol) and acetyl chloride (8.01 g, 0.10 mol) in nitrobenzene (120 ml) was treated at 0° C. with powdered anhydrous aluminium chloride (15.59 g, 0.11 mol) over a period of 30 minutes. After stirring at room temperature overnight, the reaction mixture was treated with a mixture of ice (50 g) and concentrated hydrochloric acid (20 ml). The mixture was steam distilled until removal of nitrobenzene was complete. The residue was cooled and the product extracted into ether. The ether layers were washed, dried and concentrated to give a brown solid which was purified by column chromatography on silica gel using petroleum ether/ether mixture as eluant. The product was recrystallised from ether to give a coloured solid 5.33 g. m.p. 96°-7° C.
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