O-Methylcyclohexanone

Methyl-l-cyclohexanone, see o-Methylcyclohexanone a -Methylcyclohexene, see 1-Methylcyclohexene 1-Methyl-l-cyclohexene, see 1-Methylcyclohexene Methyl 3-(dimethoxyphosphinyloxy)crotonate, see... 

Tetrahydrobenzene, see Cyclohexene Tetrahydro-o-cresol, see o-Methylcyclohexanone Tetrahydro-1,4-dioxin, see 1,4-Dioxane Tetrahydro-p-dioxin, see 1,4-Dioxane Tetrahydro-1,4-isoxazine, see Morpholine Tetrahydro-1,4-oxazine, see Morpholine Tetrahydro-p-isoxazine, see Morpholine Tetrahydro-2//-l,4-oxazine, see Morpholine... 

SYNS 2-METHYL-CYCLOHEXANON (GERMAN, DUTCH) o-METHYLCYCLOHEXANONE 1-METH-YLCYCLOHEXAN-2-ONE 2-METILCICLOESANONE (ITALIAN)... 

METHYLCYCLOHEXANONE or o-METHYLCYCLOHEXANONE or 1-METHYL-CYCLOHEXAN-2-ONE (583-60-8) Forms explosive mixture with air (flash point 118°F/48°C cc). Violent reaction with oxidizers, aldehydes, nitric acid, perchloric acid. A variety of unstable peroxides may be formed from the reaction with hydrogen peroxide. Incompatible with aliphatic amines, strong bases, hydrogen peroxide, perchloric acid. Attacks some plastics, rubber, and coatings. 

Note in one of the previous examples that alkylation of 2-methylcy hexanone leads to a mixture of products because both possible enolate it are formed. In general, the major product in such cases occurs by alkj tion at the less hindered, more accessible position. Thus, alkylation o methylcyclohexanone occurs primarily at C6 (secondary) rather than at (tertiary). 

Allylation of simple ketone is not possible under usual conditions, but the reaction can be carried out under selected conditions. Asymmetric allylation of the chiral racemic o -methylcyclohexanone 161 with allyl carbonate proceeded in the presence of LDA as a base with or without MesSnCl as a Lewis acid at room temperature to provide the allylated ketone 162 in very high yield with 82 % ee when (5,5)-Trost L-1 was used. The choice of base is crucial, and it was claimed that no reaction took place when Na or K bases were used in this reaction [57]. Asymmetric allylation of a-aryl and heteroaryl ketones has been carried out. Asymmetric allylation of 2-indolylcyclohexanone 163 took place at 0 C to give the the allyl ketone in 82 % yield with 84 % ee. In this reaction, NaHMDS was used as a base and Trost L-2 as chiral ligand [58]. Asymmetric allylation of the tetralone 164 with allyl acetate was carried out using Trost L-6 in the presence of CS2CO3 to provide the allylated ketone with 91 % ee in 90% yield [59]. 

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