What steps are used to prepare 1-methylcyclohexanol from cyclohexene?

To prepare 1-methylcyclohexanol from cyclohexene, we can follow these key steps:

1. Hydroboration-Oxidation: Begin with the hydroboration of cyclohexene using diborane (B2H6) in a THF solution. This reaction adds a boron atom to the less substituted carbon of the double bond, resulting in an organoborane intermediate.
2. Oxidation: Next, oxidize the organoborane with hydrogen peroxide (H2O2) in the presence of sodium hydroxide (NaOH). This reaction replaces the boron with a hydroxyl group, yielding cyclohexanol.
3. Methylation: Finally, to form 1-methylcyclohexanol, perform a nucleophilic substitution reaction. Treat cyclohexanol with methyl iodide (CH3I) and a strong base like potassium tert-butoxide (KOtBu). This step generates the desired product by introducing the methyl group onto the cyclohexanol structure.

These steps together lead to the synthesis of 1-methylcyclohexanol from cyclohexene, each reaction progressively adding functional groups and converting the starting material into the target alcohol.