Propanal → 4-Nitro-3-hexanol

Air in a reaction vessel was replaced with nitrogen, and 1-nitropropane (8.93 ml, 100 mmol) and dehydrated tetrahydrofuran (dry-THF) (50 ml) were added to the vessel. Then, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1.5 ml, 10 mmol) was added to the mixture. After that, propionaldehyde (4.68 ml, 100 mmol) was added to the mixture while being was cooled on an ice bath. After the mixture had been stirred at room temperature for 10 hours, ethyl acetate (100 ml) was added to the mixture, and was washed with dilute hydrochloric acid, water, and a saturated salt solution, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, whereby 4-hydroxy-3-nitrohexane was obtained (12.33 g, 84% yield).