ARYLOXYALKYL COMPOUNDS AND THEIR PREPARATION

1443612 Aryloxyalkyl compounds STERLING DRUG Inc 11 July 1974 [23 July 1973] 30800/74 Heading C2C Compounds of formula where Alk is alkylene (3-10 C) and with 3-7 C atoms between the terminal bonds, R is alkanoyl (2-6 C) R<SP>1</SP> is alkanoyl (2-6 C) or carboalkoxy (2-6 C) and Ar is phenyl or phenyl substituted by 3,4-methylendioxy or one to three monovalent substituents selected from alkyl (1-4 C), alkoxy (1-4 C), halogen, trifluoromethyl, trifluoromethoxy, hydroxy, benzyloxy, carboxy, carboalkoxy (2-4 C), acyloxy (1-10 C), dialkylamino (alkyl 1-4 C) dialkylaminoalkoxy (alkyl 1-4 C, alkoxy 2-4 C), e.g. where R and R<SP>1</SP> are both propionyl and Ar is 3-4 methylenedioxyphenyl, 4-hydroxyphenyl, 4-benzyloxyphenyl, halophenyl alkoxyphenyl, phenyl and dialkylamino, are prepared by condensing a compound in an inert solvent under anhydrous conditions, with an alkali metal salt or heavy metal chelate RR<SP>1</SP>CH 2 or with an alkali metal salt MO-Ar (M is alkali metal) and Ar has above meaning except where Ar does not include phenyl substituted by hydroxy or acyloxy, and X is bromine or iodine. In addition the compound obtained when the phenyl is benzyloxy group substituted may be hydrolysed, acylated and further hydrolysed. Examples describe the preparation of many substituted compounds which include 4-[4-(3,4- methylenedioxyphenoxy)butyl] - 3,5 - heptadione and the pentyl, hexyl, propyl and heptyl derivatives, 4 - [6 - (p - hydroxyphenoxy)hexyl- and 7 - heptyl - ] - 3,5 - heptanedione, 4 - [6 - pbenzyloxyphenoxy)hexyl]- and 4 - [7 - pbenzyloxyphenoxy)heptyl), 4 - [6 - (p - chlorophenoxy)hexyl), 4 - [6 - p - methoxyphenoxy) hexyl), 4 - (6 - phenyloxyhexyl), 4 - [6 - (mdimethylaminophenoxy) hexyl)-, 4 - [7 - (mdimethylaminophenoxy) heptyl]-, 4 - [6 - (2- chloro - 4 - methoxyphenoxy)hexyl)-, 4- [7 - (p - carbethoxyphenoxy)heptyl]-, 4 - [7 - (p - carboxyphenoxy) heptyl]-, 4 - {6 - [p - (2- diethylaminoethoxy) phenoxy]hexyl} and 4- [6 - (p - benzoyloxy - phenoxy)hexyl] - 3,5- heptanediones. The compounds have anti-viral activity and inhibit the maturation of anthropods. Conventional additives may be used to formulate solutions emulsions, suspensions dusts and sprays or they may be used in ointments or creams.