Chemical Properties
pale yellow to beige powder
Uses
1,3-Cyclohexanedione can be used as a building block in the synthesis of:
- 9-substituted 1,8-dioxo-xanthenes by reacting with unactivated aldehydes via aldol condensation/ Michael addition reaction.
- [(1,2,3-triazol-4-yl)methoxy-phenyl]-2H-indazolo[2,1-b]phthalazine-trione derivatives by treating with phthalhydrazide, aromatic propargyloxy aldehydes, and azides via a four-component condensation reaction.
It can be also used to prepare 2-substituted adducts, which are important intermediates for the synthesis of ?-enaminones , polyhydroquinoline derivatives , 1,8-dioxo-dodecahydroxanthenes , spirocyclopentanols , oxathioles , and triquinanes.
Uses
1,3-Cyclohexanedione is used in organic synthesis and pharmaceutical intermediates. It is the intermediate of herbicides sulcotrione and nitrosulfonone. It is also nitisinone intermediate.
Definition
ChEBI: 1,3-Cyclohexanedione is a cyclohexanedione carrying oxo substituents at positions 1 and 3. It is a beta-diketone and a cyclohexanedione.
Synthesis Reference(s)
The Journal of Organic Chemistry, 30, p. 3206, 1965
DOI: 10.1021/jo01020a506
Purification Methods
Crystallise the dione from *benzene. Dissolve ~50g of the diol in 140mL of *C6H6 under N2, cool, collect the solid and dry it in a vacuum desiccator overnight. It is unstable and should be stored under N2 or Ar at ~0o. [Thompson Org Synth Coll Vol III 278 1955, Beilstein 7 IV 1985.]
