20074-80-0

14273-86-0

20074-80-0

Example 53: Synthesis of 5-Chloropentanal Reactants and amounts: - Methyl-5-chlorovalerate (methyl 5-chlorovalerate): 3.5 mL (23.6 mmol, 150.61 g/mol, 1 equiv) - DIBALH (1 mol/L in toluene): 30 mL (30 mmol, 142.22 g/mol, 1.27 eq.) - Toluene: 130 mL Operating Procedure: 1. dissolve methyl 5-chlorovalerate in toluene (130 mL) and cool the solution to -78°C. 2. Slowly add DIBALH solution (30 mL, 30 mmol) dropwise over 1 hr. 3. after completion of the dropwise addition, continue to stir the reaction mixture at -78 °C for 3 hours. 4. Quench the reaction by dropwise addition of 6N hydrochloric acid (50 mL). 5. Gradually warm the reaction mixture to room temperature. 6. Separate the organic and aqueous layers and wash the organic layer twice with water. 7. The organic layer was dried with anhydrous sodium sulfate, followed by partial evaporation of the solvent. 8. 5-Chlorovaleraldehyde was obtained as a clear colorless liquid in 49% yield as confirmed by NMR analysis. 9. The product solution was stored at 4 °C under argon protection and used directly in the subsequent reaction without further purification.