Octanoyl chloride → HCID 3425108, compound

Participants

Reaction Steps

Into a 500 mL two-neck flask, dodecylamine (18.69 g) and DMAP (N,N-dimethyl-4-aminopyridine) (3.67) were added and nitrogen substitution was carried out. Subsequently, dichloromethane (150 mL) and potassium carbonate (16.67 g) were added to this. In a state in which this flask was cooled in an ice bath, a solution obtained by mixing dichloromethane (150 mL) and octanoic acid chloride (17.94 g) was dropwise added. After the dropwise addition was finished, the temperature was raised to room temperature, and the reaction was carried out for 4 hours. The end of the reaction was confirmed by gas chromatography, and 50 mL of saturated aqueous solution of ammonium chloride was added. After the resultant was stirred for 10 minutes, extraction was carried out with dichloromethane (100 mL), and the obtained organic phase was washed with 1M aqueous solution of hydrochloric acid (50 mL), saturated aqueous solution of sodium hydrogencarbonate (50 mL), and saturated aqueous solution of sodium chloride (50 mL). Removal of the solvent by reduced-pressure distillation was carried out using an evaporator, and recrystallization was carried out with dichloromethane-hexane. The yield of the object N-dodecyloctanoic acid amide was 89% (20.13 g, 89.42 mmol) in terms of dodecylamine.

Provenance & Evidence