GB1359095A - Bis-stilbene compounds - Google Patents

Abstract

1359095 4,4<SP>1</SP>-Bis-stilbene diphenyl derivatives CIBA-GEIGY AG 3 March 1972 [5 March 1971] 10056/72 Addition to 1247934 Heading C2C [Also in Divisions C3 C5 and D1] The invention comprises compounds of the Formula I: wherein R 1 denotes C 5 -C 18 alkyl, C 2 -C 20 substituted alkyl or C 3 -C 4 alkenyl, X 1 denotes hydrogen, halogen, C 1 -C 4 alkoxy, C 3 -C 4 alkenyl or C 1 -C 4 alkyl, Y 1 denotes hydrogen, halogen, C 3 -C 4 alkenyl or C 1 -C 4 alkyl, a denotes hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, M represents hydrogen, alkali metal, alkaline earth metal ammonium or amine salt cation, n denotes 1 or 2 and W 1 and W 2 independently represent hydrogen, halogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy groups. The novel compounds of the invention are prepared by reacting about 1 mole equivalent of a compound of Formula II: with about 1 mol. equivalent of each of the compounds of Formula IIIa and IIIb: wherein one of Z 1 or Z 2 represents the grouping -CH=O while the other represents a group having one of the following formulµ: wherein R is an optionally substituted alkyl radical preferably C 1 -C 6 alkyl, aryl, cycloalkyl or aralkyl group. The preferred reaction is between a 4,4<SP>1</SP>-diphosphono biphenyl and appropriately substituted benzaldehydes. The benzaldehyde ethers, e.g. corresponding to Formula IIIa, in which Z 2 is CHO, above may be prepared by reaction of the corresponding hydroxy aldehyde with an appropriate bromo compound in the presence of a base, or, for the preparation of ethers in which the group is further substituted by a sulphonic group, by reacting the hydroxy aldehyde with a sultone, again in the presence of a base, e.g. sodium hydride or sodium methylate, potassium carbonate. Compounds of Formulµ IV and V are obtained as by-products from the reaction of 4-chlorobenzaldehyde-3-sulphonic acid and 2- benzyloxy - 3,5 - dichlorobenzaldehyde with 4,41-bis - (dimethoxyphosphonomethyl)diphenyl.