3-Methyl-2-cyclohexen-1-one

May be prepared by acid hydrolysis and decarboxylation of the corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-l-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric acid.

CLEAR VERY SLIGHTLY YELLOW TO BROWN LIQUID

3-Methyl-2-cyclohexen-1-one is a nonaromatic cyclic ketone with a medicinal, phenolic, mild cherry aroma

Reported found in oil of Mentha pulegium, cocoa, coffee, filbert, sweet corn, dried bonito, katsuobushi, wild rice and clam. Also produced by some animals in vivo

3-Methyl-2-cyclohexen-1-one was used in the synthesis of 19-nor-1α, 25-dihydroxyvitamin D(3) derivatives. It was also used in sex pheromone of the Douglas-fir beetle. Used in nut flavor.

3-Methyl-2-cyclohexenone is an insect sex pheromone of the Douglas-fir beetle. It can be used as a starting material:

• In the total synthesis of (?)-ar-tenuifolene, a naturally occurring aromatic sesquiterpene.
• To synthesize an organic building block 2-trimethylsilyl-3-methyl-cyclohexenone.
• In the total synthesis of natural diterpenoids (+)-taiwaniaquinone H and (+)-dichroanone.

ChEBI: 3-Methyl-2-cyclohexen-1-one is a cyclic olefin.

By acid hydrolysis and decarboxylation of the corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-1-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric acid.

Aroma characteristics at 2.0%: sweet, nutty, phenolic, walnut, fruity, almond and benzoin

Taste characteristics at 50 ppm: nutty, musty, phenolic and woody with grain-like nuances.

Journal of the American Chemical Society, 101, p. 494, 1979 DOI: 10.1021/ja00496a044
The Journal of Organic Chemistry, 42, p. 1349, 1977 DOI: 10.1021/jo00428a017
Tetrahedron Letters, 17, p. 3, 1976