Benzaldehyde → Nonanal, 2-(phenylmethylene)-

Participants

Reaction Steps

The alcohol was prepared by hydrogenation of a-heptylcinnamaldehyde exactly as in Example 1. -Heptylcinnamaldehyde was prepared as follows: To a mixture of 53.8 g (0.50 mole) benzaldehyde 50 ml ethanol and 25 ml 10% NaOH at reflux were added 56.8 g (0.40 mole) nonanal dropwise over 20 min. Halfway through the addition of nonanal an additional 25 ml 10% NaOH were added. After two hours at reflux the mixture was cooled, diluted with 100 ml 30°-60° petroleum ether, washed once with 50 ml 5% HCl, once with saturated NaCl brine, filtered through 4A molecular sieves, stripped and fractionally distilled, bp 135°-150°/0.15 mm, to give 56.1 g (61%) whose IR showed aromatic CH stretch from 3000-3100 cm-1, aldehyde CH at 2705 cm-1, and an aldehyde C=0 at 1706 cm-1.

Provenance & Evidence