Benzophenone → Nonanal

Participants

Reaction Steps

Using a Fisher-Porter bottle, 0.86 g (37.4 mmol) of solid sodium metal and 2.91 g (16 mmol) of benzophenone were added to 40 ml of dry, degassed THF under N2 flow. The reaction turned blue, characteristic of the ketyl. The Fisher-Porter bottle was then pressured up to 43 psi over atmospheric with CO and the whole reaction stirred vigorously using a magnetic stirrer at 120°. At this pressure THF can reach temperatures in excess of 100° before boiling. The reaction was cooled to 60° and 2.25 ml (16.8 mmol) of Fe(CO)5 was added. A white precipitate remained after addition of n-hexane. Washing the white precipitate and pumping to dryness gave a product that yielded 92% nonanal based on 214 MW for Na2Fe(CO)4. The product of this example was not solvated.

Provenance & Evidence