1,3-Cyclohexanedione


1,3-Cyclohexanedione is an organic compound with the formula 42. It is one of three isomeric cyclohexanediones. It is a colorless compound that occurs naturally. It is the substrate for cyclohexanedione hydrolase. The compound exists mainly as the enol tautomer.

Synthesis, structure, and reactivity

1,3-Cyclohexanedione is produced by semi-hydrogenation of resorcinol:
1,3-Cyclohexanedione exists in solution as the enol. It reacts under acid catalysis with alcohols to 3-alkoxyenones.
Its pKa is 5.26. Treatment of the sodium salt of the enolate with methyl iodide gives 2-methyl-1,3-cyclohexanedione, which despite the name, also exists predominantly as the enol.

Derivatives

, 5,5-dimethyl-1,3-cyclohexanedione is a well established reagent.
Several herbicides are formal derivatives of 1,3-cyclohexanedione. Examples of commercial products include cycloxydim, clethodim, tralkoxydim, butroxydim, profoxydim, mesotrione and quizalofop-P-ethyl.