2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Pyrene-4-carbaldehyde

Participants

Reaction Steps

1,2,3,6,7,8-Hexahydro-4-pyrenecarbaldehyde (19A, 11.81 g, 50 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (Aldrich, 39.75 g, 0.175 mol) were refluxed for 4 h in 1 L of PhCH3. The reaction mixture was cooled and then filtered. The filtrate was washed with 2N NaOH (3×500 mL), satd. NaCl solution (2×500 mL), dried (Na2SO4), and passed through a plug of SiO2 (200 g). The solvent was then removed to give a bright yellow solid that was dried at 50° to give 8.91 g (77%) of 4-pyrenecarbaldehyde which was used without further purification. An analytical sample had mp 172°-174°, (CH2Cl2 /hexane), (C, H), (lit. mp 177°-179°, Y. E. Gerasimenko and I. N. Shevcbuk, Zh. Org. Khim. 4 2198 (1968)).

Provenance & Evidence