6-Hydroxy-2-naphthaldehyde

6-Hydroxy-2-naphthaldehyde is a fluorophore characterized by a simple molecular structure and photophysical properties. It serves as a precursor in the preparation of the fluorescent probe AENO by coupling with potassium allyltrifluoroborate in the presence of ammonia solution[4].

A stirring bar, 0.35 g (2.01 mmol) of 6-hydroxy-2-naphthylcarbinol and 20 mL of N, N-dimethylformamide were introduced into a 100 mL flask to form a homogenous mixture. This mixture was added with 3.5 g (36.94 mmol) of electrolytic manganese dioxide (FMH, Tosoh, purity: 91.77 per cent) and vigorously stirred for 16 hours while the mixture was maintained at 20°C. The reaction mixture was analyzed by using liquid chromatography. As a result, it was found that the conversion of the 6-hydroxy-2-naphthylcarbinol was 92.3 per cent, and the yield of the 6-hydroxy-2-naphthaldehyde was 87 percent.

[1] Patent: CN105111054,  2017,  B. Location in patent: Paragraph 0088; 0089; 0090
[2] Patent: WO2006/82245,  2006,  A1. Location in patent: Page/Page column 156
[3] Patent: US2003/229120,  2003,  A1. Location in patent: Page 52
[4] Xu, J., Zhang, Y., Zeng, L., Liu, J., Kinsella, J. M., & Sheng, R. (2016). A simple naphthalene-based fluorescent probe for high selective detection of formaldehyde in toffees and HeLa cells via aza-Cope reaction. Talanta, 160, 645–652. https://doi.org/10.1016/j.talanta.2016.08.010