摘要 |
1283944 Substituted alkyl halides and cyanides; organomagnesium compound CIBAGEIGY AG 25 Sept 1969 [11 Oct 1968 6 Nov 1968 8 May 1969 21 Aug 1969] 45827/71 Divided out of 1283943 Headings C2C and C2J The invention comprises novel substituted alkyl halides and cyanides of the formula in which X is halogen or CN; R is a 1-cycloalkenyl radical; Ph is o- or p-phenylene; and R 1 and R 2 each represent H or a monovalent aliphatic or araliphatic hydrocarbon radical, or together a divalent aliphatic or araliphatic hydrocarbon radical, with the exception of the compound of the above formula in which R is 1-cyclohexenyl, Ph is p-phenylene, R 1 is CH 3 , R 2 is H and X is halogen or CN, and their preparation. The cyanides are obtained by treating the corresponding halides, resulting from the halogenation of the corresponding alcohols, with for example, potassium cyanide. 1 - Hydrozy - 1 - [p - (1 - cycloheptenyl)phecyl]. 1-hydroxy-1-[p- (1 -cyethane, clopentenyl)phenyl] ethane, 1 - hydroxy - 1 - [p - (6 - methylcyclohexenyl)phenyl]ethane, 1 - hydroxy - 1 - [p - (2- methyloyclohexenyl)phenyl]ethane, 1 - hydroxy- 1- [p- (4 - methylcyclohexenyl)phenyl]ethane, and 1 - hydroxy - 1 - [p - (4 - methoxycyclohexenyl)- phenyl]ethane are obtained by reducing the appropriate acetophenones, resulting from the dehydration and hydrolysis of 2-[p-(1-hydroxycycloheptyl)phenyl]-2-methyl-1,3-dioxolane, 2-[p- (1 - hydroxycyclopentyl)phenyl]- 2 - methyl - 1,3- dioxolane, 2 - [p - (2 - methyl - 1 - hydroxycyclohexyl)phenyl] - 2 - methyl - 1,3 - dioxolane, 2 - [p- (4 - methyl - 1 - hydroxycyclohexyl)phenyl]- 2- methyl - 1,3 - dioxolane, and 2 - [p - (4 - methoxy- 1 - hydroxycyclohexyl)phenyl]- 2 - methyl - 1,3- dioxolane respectively, which are in turn prepared by hydrolysing the products resulting from the reaction between the appropriate cycloalkanone and the Grignard reagent prepared by reacting magnesium chips with a solution of 2 - (p - bromophenyl) - 2 - methyl - 1,3 - dioxolane in absolute tetrahydrofuran. |