Pyrans,their analogs,and related compounds

Reaction of 4, 4-dichloroflavine (I) with sulfurylchloride affords 2, 3, 3, 4, 4-pentachloroflavan (II). Hydrolysis of II gives 2-hydroxy-3, 3-dichloro-4-flavanone (III), while alcoholysis with aqueous alcohols yields 2-alkoxy-3,3-dichloro-4-flavanones (IVa, b). Treatment of III with SOCl₂ gives 2,3,3-trlchloro-4-flavanone (V), which with caustic alkali or sodium ethoxide is converted into o-(1-phenyl-2, 2-dichlorovinyloxy)benzoic acid (VIc) or its ethyl ester (VIb), respectively.For Part XLII, see [7].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1167–1170, September, 1970.