C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/367, 260/361
C07D 493/08 (2006.01)
Patent
CA 1255687
A B S T R A C T PROCESS FOR PREPARING OXABICYCLOALKANE COMPOUNDS The invention provides a process for preparing an oxabi- cycloalkane compound of formula Image (I) wherein R1 is a hydrogen atom or C1-6 alkyl group option- ally substituted by up to 3 fluorine, chlorine and/or bromine atoms; R2 is a hydrogen atom or a C1-6 straight-chain alkyl group; R3 is a hydrogen atom; a C1-10 alkyl group; a cyano group; an alkyl group substituted by one or more halogen atoms or by a hydroxy group, a cyano group, a C1-6 alkoxy group, an aryl- oxy group, a C1-6 alkylsulphonyl group, an arylsulphonyl group an aralkylsulphonyl group, an azido group, a C1-6 alkoxycar- bonyl group, an aralkoxy carbonyl group, a hydroxycarbonyl group, a phosphoryl group, a phosphoryloxy group, or an amine oxide, carbamoyl or thiocarbamoyl group in which each nitrogen is substituted by hydrogen or by 1 or 2 C1-4 alkyl groups; a C2-4 alkenyl or alkynyl group; an aryl or aralkyl group, each containing from 6 to 11 carbon atoms including 1 to 4 carbon atoms in the alkyl portion and optionally ring substi- tuted by one or more fluorine, chlorine and/or bromine atoms or by a C1-2 alkyl or alkoxy group, each optionally substi- tuted by one or more fluorine and/or chlorine atoms; a group -CSNH2; a group -CO2R6 or -CON(R6)2 in which R6 is a hydrogen atom or a C1-6 alkyl group; or a C1-6 acyl group or an oxime or an acetal derivative of said acyl group; each R4 is independently a hydrogen atoms; an alkyl group optionally substituted by up to 3 halogen atoms; a hydroxy group; or a C1-4 alkoxy group; and each R5 independently is a hydrogen atom, a C1-4 alkyl group optionally substitu- ted by up to 3 halogen atoms; or a chlorine or bromine atom; which process comprises treating a liquid-phase mixture of a compound of formula Image (II) wherein R1, R2, R3, R4 and R5 are as defined above, an aldehyde containing at least two carbon atoms and an organic solvent, with oxygen in the presence of a catalyst which is soluble in the reaction mixture and which comprises a pra- seodymium compound and at least one compound of molybdenum, niobium, tantalum, tungsten, uranium and vanadium.
459595
Shell Canada Limited
Smart & Biggar
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