Menthone 5-methyl-2- cyclohexanone

A qualitative study of 2, 3, and 4-methyl cyclohexanones as well as menthone (XX) has been carried out (1). 

Baeyer-Villiger oxidation of menthone [2-methyl-5-(l-methylethyl)cyclohexanone]. Alternatively, one may first convert menthone into the silyl enol ether B and cleave its C=C double bond with ozone to obtain a bifunctional compound, which exhibits a trimethylsilyl ester and an a-methoxyhydroperoxide. The latter is reduced with NaBLLi to the hydroxylated silyl ester C. The hydroxycarboxylic acid is obtained therefrom by acid-catalyzed hydrolysis. It cyclizes spontaneously to give lactone D. 

Reduction of a series of cyclohexanones (2- and 4-methyl, 4-isopropyl, 4-r-butyl and 3,3,5-trimethyl), both in the presence and absence of proton donors gave a 99 1 ratio of equatorial to axial alcohol. For 3-methylcyclohexanone the ratio was 94 6. Also, reduction of menthone (4) affords a 97 3 ratio of equa-... 

All measurements in acetone solution. b l70-enriched acetone was used as precursor. In 2-butanone. Jln 3-methyl-2-butanone. In 3,3-dimethyl-2-butanone. fIn CFCI,/CC14. In trifluoroacetone. hInCCl4. In gas phase. JIn CD2Cl2. kIn Ar/O, matrix. In cyclohexanone. "In 2-methylcyclohexanone. "In 3-methylcyclohexanone. In 4-methylcyclohexanone. In menthone. Partial data in the range 1750-500 cm... 

Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S-trans)-. See l-Menthone Cyclohexanone, 5-methyl-2-(1-methylethylidene)-, (R)-. See d-Pulegone... 

Synonyms Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S-trans)- (1R,4S)-(-)-p-Menthan-3-one L-Menthan-3-one l-p-Menthan-3-one p-Menthan-3-one (-)-Menthone 1-Methyl-4-isopropylcyclohexan-3-one (2S-trans)-5-Methyl-2-(1 -methylethyl) cyclohexanone (-)-5-Methyl-2-(1-methylethyl) cyclohexanone... 

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