Methanol → Cinnamoylbenzene

Participants

Reaction Steps

Potassium hydroxide (18.2 g, 325 mmol) was dissolved in 100 mL of H2 O, and 100 mL of methanol was added. 2-Acetyl-6-bromopyridine (65 g, 325 mmol) and (68 g, 650 mmol) of p-anisaldehyde were dissolved together in 400 mL of methanol, and the solution was poured into the KOH solution. Precipitation of product began within a few minutes, and the reaction was allowed to stand at room temperature overnight. The precipitate was collected, washed with isopropanol, and dried to yield 79 g (76%) of the product as a yellow solid, mp 100°-102° C. FDMS (m/e) 317M. An aliquot was purified by column chromatography on Woelm Silica gel, elution with 100% dichloromethane. Anal. Calcd for C15H12 BrNO2 : C, 56.63; H, 3.80; N, 4.40. Found: C, 56.66; H, 3.87; N, 4.41. The NMR and IR spectra were consistent with the assigned structure and the product was homogeneous by TLC.

Provenance & Evidence