Synthesis of .alpha.-nitrosoketal dimers
AssigneeAllied Chemical Corporation
InventorsMilorad M. Rogic, Michael D. Swerdloff, Timothy R. Demmin
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Abstract
Ketals of .alpha.-oximinoketones and methods for the preparation of these compounds including intermediates are described. The compounds disclosed include both .alpha.-oximinoketals and cyclic ketals of .alpha.-oximinoketones. Also disclosed is a class of .alpha.-nitrosoketal dimers produced during the synthesis of the corresponding .alpha.-oximinoketals and the method for their preparation.
Claims5
A process for the production of an .alpha.-nitrosoketal dimer of the formula ##STR37## wherein R.sup.1 and R.sup.2 are selected from the group consisting of C.sub.1 -C.sub.10 alkyl or phenyl and/or combinations thereof, or in combination together R.sup.1 and R.sup.2 are a part of the C.sub.5 -C.sub.12 cyclic structures, and
- R.sup.3 and R.sup.4 are independently selected from the group consisting of C.sub.1 -C.sub.10 alkyl, cyclohexyl and C.sub.1 -C.sub.4 alkyl substituted cyclohexyl radicals, comprising the steps of:
- a. nitrosating, in the presence of a catalytic amount of a suitable acid and at a temperature of between about -70.degree. and 25.degree. C and at a pressure of between about one atmosphere and 200 psi, an alkoxyalkene of the formula ##STR38## wherein R.sup.1 and R.sup.2 are selected from the group consisting of C.sub.1 -C.sub.10 alkyl, phenyl and wherein both R.sup.1 and R.sup.2 are part of a C.sub.5 -C.sub.12 carbo-cyclic structure, and R.sup.3 is selected from the group consisting of C.sub.1 -C.sub.10 alkyl, cyclohexyl and C.sub.1 -C.sub.4 alkyl substituted cyclohexyl;
- with at least one molar equivalent of an alkyl nitrite of the formula
- R.sup.4 ONO
- wherein R.sup.4 is selected from the group consisting of C.sub.1 -C.sub.10 alkyl, cyclohexyl and C.sub.1 -C.sub.4 alkyl substituted cyclohexyl;
- and
- b. isolating the dimer thus formed.
The process for the production of 1,1-dimethoxy-2-nitrosocyclohexane dimers comprising the steps of (a) nitrosating 1-methoxycyclohexene with 2-10 molar equivalents of methyl nitrite in the presence of 1.10-2.0 mole % of ethyldimethoxycarbonium fluoroborate catalyst at temperature between -30.degree. and 25.degree. C., and pressure of one atmosphere to 200 psi and;
- b. evaporation of the excess of methyl nitrite, followed by addition of petroleum ether or other inert solvent, and filtration of the product.
Dependencies are inferred from the claim text.