1-bromo-4-methylheptane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This was prepared from compound (1) in 70% yield by hydrogenation over platinum oxide in glacial acetic acid: b.p. 67°-70° C. at 8.5 mm; NMR (CDCl3) 0.86 (t, CH3CH2), 0.87 (d, CH3CH), 3.40 (m, 2H, CH2CH2Br)). The IR and NMR spectra of the compound were in complete agreement with the assigned structure and reported values.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: This was prepared from compound (1) in 70% yield by hydrogenation over platinum oxide in glacial acetic acid: b.p. 67°-70° C. at 8.5 mm; NMR (CDCl3) 0.86 (t, CH3CH2), 0.87 (d, CH3CH), 3.40 (m, 2H, CH2CH2Br)). The IR and NMR spectra of the compound were in complete agreement with the assigned structure and reported values.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The novel synthesis of racemic 6,12-dimethylpentadecan-2-one is shown in FIG. 4 and described in detail below in Example 2. Briefly, the synthesis of racemic 6,12-dimethylpentadecan-2-one was initiated by the reaction of methylcyclopropyl ketone with n-propylmagnesium bromide. The intermediate tertiary carbinol was isomerized to the homoallylic bromide (1) with hydrobromic acid. The allic bromide (1) was reduced to 1-bromo-4-methylheptane (2) by hydrogenation with PtO2. The saturated bromide (2) was converted to the corresponding organocopper reagent which was reacted with methyl vinyl ketone in the presence of tri-n-butyl phosphine to produce 8-methylundecan-2-one (3). A Wittig reaction between the C-12 methylketone (3) and ethylene ketal pentan-2-one phosphonium salt (4), produced a mixture of the Z and E isomers of the ethylene ketal of 6,12-dimethyl-(5) (15% yield). The unsaturated ethylene ketals were hydrogenated and then subjected to acid hydrolysis to produce 6,12-dimethylpentadecan-2-one (7). The final product was purified by high-performance liquid chomatography (HPLC) and GLC.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The novel synthesis of racemic 6,12-dimethylpentadecan-2-one is shown in FIG. 4 and described in detail below in Example 2. Briefly, the synthesis of racemic 6,12-dimethylpentadecan-2-one was initiated by the reaction of methylcyclopropyl ketone with n-propylmagnesium bromide. The intermediate tertiary carbinol was isomerized to the homoallylic bromide (1) with hydrobromic acid. The allic bromide (1) was reduced to 1-bromo-4-methylheptane (2) by hydrogenation with PtO2. The saturated bromide (2) was converted to the corresponding organocopper reagent which was reacted with methyl vinyl ketone in the presence of tri-n-butyl phosphine to produce 8-methylundecan-2-one (3). A Wittig reaction between the C-12 methylketone (3) and ethylene ketal pentan-2-one phosphonium salt (4), produced a mixture of the Z and E isomers of the ethylene ketal of 6,12-dimethyl-(5) (15% yield). The unsaturated ethylene ketals were hydrogenated and then subjected to acid hydrolysis to produce 6,12-dimethylpentadecan-2-one (7). The final product was purified by high-performance liquid chomatography (HPLC) and GLC.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The novel synthesis of racemic 6,12-dimethylpentadecan-2-one is shown in FIG. 4 and described in detail below in Example 2. Briefly, the synthesis of racemic 6,12-dimethylpentadecan-2-one was initiated by the reaction of methylcyclopropyl ketone with n-propylmagnesium bromide. The intermediate tertiary carbinol was isomerized to the homoallylic bromide (1) with hydrobromic acid. The allic bromide (1) was reduced to 1-bromo-4-methylheptane (2) by hydrogenation with PtO2. The saturated bromide (2) was converted to the corresponding organocopper reagent which was reacted with methyl vinyl ketone in the presence of tri-n-butyl phosphine to produce 8-methylundecan-2-one (3). A Wittig reaction between the C-12 methylketone (3) and ethylene ketal pentan-2-one phosphonium salt (4), produced a mixture of the Z and E isomers of the ethylene ketal of 6,12-dimethyl-(5) (15% yield). The unsaturated ethylene ketals were hydrogenated and then subjected to acid hydrolysis to produce 6,12-dimethylpentadecan-2-one (7). The final product was purified by high-performance liquid chomatography (HPLC) and GLC.