Process for the production of acylated 1,3-dicarbonyl compounds
AssigneeStauffer Chemical Company
InventorsJames B. Heather, Pamela D. Milano
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Abstract
An acylated 1,3-dicarbonyl compound is produced by rearrangement of the corresponding enol ester in the presence of a cyanide source. In one embodiment the cyanide source is employed with a molar excess of a moderate base, with respect to the enol ester. In another embodiment, the cyanide source is a stoichiometric amount, with respect to the enol ester, of potassium or lithium cyanide and a catalytic amount of a crown ether is used.
Claims49
A process for producing an acylated cyclical 1,3-dicarbonyl compound by rearrangement of the corresponding enol ester in which the rearrangement is conducted in the presence of a cyanide source which is an alkali metal cyanide, a cyanohydrin of a methyl alkyl ketone having from 1 to 4 carbon atoms in the alkyl group, benzaldehyde cyanohydrin, cyclohexanone cyanohydrin, a cyanohydrin of a C.sub.2 -C.sub.5 aliphatic aldehyde, lactonitrile, a lower alkyl silyl cyanide, potassium ferricyanide, or hydrogen cyanide.
A process for producing a benzoylated cyclical 1,3-dicarbonyl compound by rearrangement of the corresponding enol ester in which the rearrangement is conducted in the presence of a cyanide source.
A compound having the formula ##STR46## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are independently hydrogen or C.sub.1 -C.sub.4 alkyl or
- R.sup.1 or R.sup.3 is ##STR47## in which R.sub.a is C.sub.1 -C.sub.4 alkyl;
- phenyl, optionally substituted by from 2 to 5 methyl groups;
- or in which R.sup.1 and R.sup.2, or R.sup.3 and R.sup.4, taken together are C.sub.2 -C.sub.5 alkylene;
- R.sup.7 is halogen;
- R.sup.8, R.sup.9 and R.sup.10 independently are hydrogen;
- alkyl;
- C.sub.1 -C.sub.4 alkoxy, trifluoromethoxy;
- cyano;
- nitro;
- C.sub.1 -C.sub.4 haloalkyl;
- C.sub.1 -C.sub.4 alkylthio;
- phenoxy;
- or substituted phenoxy in which the substituent is halogen or halomethyl or both;
- R.sub.b S(O).sub.n in which n is 0, 1 or 2;
- and R.sub.b is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, phenyl or benzyl, ##STR48## in which R.sub.c is C.sub.1 -C.sub.4 alkyl, --NR.sub.d R.sub.e in which R.sub.d and R.sub.e independently are hydrogen or C.sub.1 -C.sub.4 alkyl;
- R.sub.f C(O)-- in which R.sub.f is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl or C.sub.1 -C.sub.4 alkoxy;
- SO.sub.2 NR.sub.g R.sub.h in which R.sub.g and R.sub.h independently are hydrogen or C.sub.1 -C.sub.4 alkyl;
- or R.sup.8 and R.sup.9 taken together form a ring structure with two adjacent carbon atoms of the phenyl ring to which they are attached.
Dependencies are inferred from the claim text.