Process for preparing 2-carboalkoxy-1-indanones
AssigneeE. I. Du Pont de Nemours and Company
InventorsDonald Joseph Dumas, William Christopher Hollinsed
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Abstract
A process for the preparation of 2-carboalkoxy-1-indanones of Formula I from 1-indanones of Formula II using a dialkyl carbonate and an alkali metal alkoxide is provided. This process is superior to the prior art in that it avoids pyrophoric reagents such as sodium hydride, and proceeds in high chemical yield and product quality. The invention provides a novel process to an important intermediate in the preparation of arthropodicidal carboxanilides of commercial interest. ##STR1## wherein: R.sup.1, R.sup.2 and M are defined in the specification.
Claims6
The process for the preparation of a 2-carboalkoxy-1-indanone of Formula I:
- ##STR4## comprising reacting a 1-indanone of Formula II ##STR5## with at least one molar equivalent of a dialkyl carbonate of the formula (R.sup.2 O).sub.2 C=O in an aprotic solvent in the presence of a base MOR.sup.2 and removing alcohol R.sup.2 OH by distillation as it is formed from the reaction of the indanone of Formula I with the dialkyl carbonate
- wherein:
- R.sup.1 is selected from the group H, R.sup.3, C.sub.2 -C.sub.6 alkoxyalkyl, C.sub.2 -C.sub.6 alkylthioalkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sup.3 -C.sub.6 fluorocycloalkyl, halogen, OR.sup.3, SR.sup.3, S(O)R.sup.3, S(O).sub.2 CF.sub.3, S(O).sub.2 CF.sub.2 R.sup.3, OS(O).sub.2 R.sup.3 ;
- CO.sub.2 R.sup.2, NR.sup.3 R.sup.4, NO.sub.2, phenyl optionally substituted with 1 to 3 substituents independently selected from R.sup.5 and benzyl optionally substituted with 1 to 3 substituents independently selected from R.sup.5 ;
- R.sup.2 is C.sub.1 -C.sub.6 alkyl;
- R.sup.3 is selected from the group C.sub.1 -C.sub.6 alkyl, and C.sub.1 -C.sub.6 fluoroalkyl;
- R.sup.4 is C.sub.1 -C.sub.4 alkyl;
- R5 is selected from the group halogen, NO.sub.2, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 fluoroalkyl, C.sub.1 -C.sub.2 alkoxy C.sub.1 -C.sub.2 fluoroalkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.1 -C.sub.2 fluoroalkylthio, SO.sub.2 CF.sub.3, SO.sub.2 CF.sub.2 R.sup.3, and
- M is an alkali metal.
Dependencies are inferred from the claim text.