22428-87-1

100-39-0

2987-06-6

Synthesis of 4-(benzyloxy)cyclohexanone (14-2) Procedure: a 60% sodium hydride dispersion in mineral oil (760 mg, 23 mmol, 1.2 eq.) was slowly added to a solution of anhydrous THF (50 mL) of 1,4-dioxaspiro[4.5]decan-8-ol (14-1) (3.0 g, 19 mmol, 1.0 eq.) at 0 °C. After 6 hours of reaction, benzyl bromide (2.5 mL, 21.3 mmol, 1.1 equiv) was added dropwise to the mixture. Subsequently, the reaction mixture was stirred at room temperature overnight. After the reaction was completed, 4N HCl solution (30 mL) was added and stirring was continued for 6 hours at room temperature. The reaction mixture was neutralized with 4N sodium hydroxide solution to pH ≈ 7 and then extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by an AnaLogix automated column chromatography system using a 0 to 30% ethyl acetate/heptane gradient elution to afford the target product 14-2 (3.0 g, 77% yield) as a light yellow oil.