Uses
1-Naphthoyl chloride has been used as derivatization reagent in analysis of short-chained dodecyl alcohol ethoxylates and dodecyl alcohol by solid-phase extraction combined with dispersive liquid-liquid micro extraction method, as fluorescent labeling reagent in determination of T-2 and HT-2 toxins by HPLC with fluorescence detection, in Arndt-Eistert synthesis in the presence of trimethylsilyldiazomethane and in preparation of 2-ethyl-1-pentyl-3-(1-naphthoyl)indole.
Synthesis
General method: Method A: 1-Naphthalenecarboxylic acid (5.8 mmol) was dissolved in dry toluene (40 mL) and thionyl chloride (8.0 mmol) was added. After refluxing the reaction for 2 hours, evaporate under reduced pressure to remove the solvent and excess thionyl chloride to give 1-naphthalenecarboxylic acid as a colorless liquid in quantitative yield. Upon cooling, the product formed colorless needle-like crystals with a melting point of 18-19°C (literature value 26°C [54]). 1-Naphthalenecarbonyl chloride (5.8 mmol), triethylamine (8.7 mmol) and the corresponding substituted aniline (5.8 mmol) were dissolved in anhydrous dichloromethane (30 mL), and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was removed by evaporation under reduced pressure, the solid residue was washed with 10% hydrochloric acid solution, the crude product was recrystallized with isopropanol and decolorized by the addition of activated carbon.
References
[1] Molecules, 2014, vol. 19, # 7, p. 10386 - 10409
[2] Patent: WO2009/91324, 2009, A1. Location in patent: Page/Page column 29
[3] Organic Letters, 2005, vol. 7, # 3, p. 367 - 369
[4] Chemische Berichte, 1905, vol. 38, p. 180
[5] Chemische Berichte, 1868, vol. 1, p. 42
