Synthesis of Trialkylacetic Acids by the Anodic Oxidation of 3,3-Disubstituted-2-oxo Carboxylic Acids

Article abstract of DOI:10.1021/jo00184a013

The "non-Kolbe" electrolysis of 3,3-disubstituted-2-oxocarboxylates 1-3 in methanol produced mixtures of methyl trialkylacetates 5, trialkylacetaldehydes 6, in some cases 2-hydroxy-3,3,3-trialkylpropionic acids 7, trialkylethylenes 8, and methyl trialkylmethyl ethers 9.When one of the substituents on the 3-carbon of the 2-oxo carboxylate was phenyl 4, molecular rearrangement was not observed.In addition to products 5-9, with the exception of 7, there was obtained with 4 an alkyl phenyl ketone 10.The methyl trisubstituted acetates were saponified to the desired trialkylacetic acids.