2,6-Dimethyloct-7-en-4-one → HCID 9964216, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of dihydrotagetone (4) (3.53 g, 22.92 mmole), sodium bicarbonate (1.8 g, 21.43 mmole), sodium metaperiodate (22.84 g, 106.78 mmole), potassium permanganate (0.65 g, 4.11 mmole), alumina (0.8-1.2 g) and THF-water or acetone-water (20 mL, 1:3) was taken in a 250 ml Erlenmeyer flask fitted with a loose funnel at the top. The flask was shaken well for a while and then placed inside a microwave oven (Kenstar) operating at medium power (600 W) and irradiated for 2-20 minutes in parts. After completion of the reaction (monitored by TLC), the contents of the flask were poured into saturated solution of sodium bisulphite to destroy excess permanganate and resulting mixture was passed through a bed of Celite and further washed with aqueous acetone (40 mL×3, 3:1). The filtrate and washings were combined and the solution concentrated under reduced pressure to remove acetone. The mixture was cooled to 0 to 8° C. and acidified with dilute acid and then extracted with ethylacetate (3×25 mL). The ethylacetate layers were then combined, washed with saturated sodium bisulphite and sodium chloride (3×15 mL), dried over anhydrous sodium sulphate and then filtered. The solvent was removed to afford a crude product which was purified on silica column as above which afforded 2,6-dimethyl-4-oxo-heptanoic acid (3) in 81% yield as a viscous liquid. The physical and spectral data was found similar as above (Example II-i).

Provenance & Evidence