Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks

• Clémence Moitessier,
• Ahmad Rifai,
• Pierre-Edouard Danjou,
• Isabelle Mallard and
• Francine Cazier-Dennin

Beilstein J. Org. Chem. 2019, 15, 721–726, doi:10.3762/bjoc.15.67

• – National Council for Scientific Research – B. P. 11- 8281, Riad El Solh 1107, 2260 Beirut, Lebanon 10.3762/bjoc.15.67 Abstract 4-Methoxy-ortho-phthalaldehyde and 4-hydroxy-ortho-phthalaldehyde are potentially useful molecules for fluorimetric analysis of a variety of amines and for the elaboration of

• ; hydroxy group protection; 4-hydroxy-ortho-phthalaldehyde; ortho-phthalaldehyde; oxidation; Introduction Benzene-1,2-dicarboxaldehyde, also called ortho-phthalaldehyde (OPA) was employed in different domains such as in analytical and organic chemistry. In fact, it is one of the most commonly used

• and a quantitative yield upon its reaction with p-toluenesulfonic acid (p-TsOH). Conclusion This study presents the highest reported yield for the synthesis of 4-methoxy-ortho-phthalaldehyde (5b) and 4-hydroxy-ortho-phthalaldehyde (6). For the latter, our study highlights the necessity to protect the