General procedure: Example 3
To a reaction vessel, 510 mg (13.5 mmol) of sodium borohydride, 8 mL of tetrahydrofuran, 209 μL (1.63 mmol) of n-nonane, and 650 mg (6.8 mmol) of magnesium chloride were sequentially added, and the reaction mixture was stirred for 24 hours at room temperature. Subsequently, 9.8 mL of a tetrahydrofuran solution containing 1.11 g (9.9 mmol) of 1,3-cyclohexanedione was slowly added dropwise for 30 minutes. After the titration was completed, the reaction and post-treatment were carried out according to the method of Example 1. Upon completion of the reaction, the formation of cyclohexane-1,3-diol was confirmed by analysis in 97.5% yield. By-products included cyclohexanol (0.2%) and 2-cyclohexen-1-ol (1.2%).
