Just a small addition: in SWIMs previous reply, he talked about cinnamic acids (Perkin). It is also possible to make cinnamaldehydes, and go for the allyl isomeres (eugenol, safrol, methylchavicol). All depends on the bee: what does he want to do, and fits him best...
(translatiert auf German ::) )
Ungesättigte aromatische Aldehyde (unsaturated aromatic aldehydes) [V. Meyer and P. Jacobson, Lehrbuch der organischen Chemie, Walter de Gruyter & Co., 1923, B2 P1, p. 487-488]
Cinnamaldehyde Ph-CH=CH-CHO (propenylalbenzene) is an easy to get substance. It is a main component of "Zimmtöls" (a), which can be prepared by distilling the bark of Cinnamonium cassia and Cinnamonium ceylonicum, and by steam distilling the leaves of Cinnamonium cassia (b). The substance can be obtained in high purity by its sodiumbisulfite derivative. It can also be prepared synthetically by condensation of benzaldehyde and acetaldehyde in the presence of a weak alkaline solution:
Ph-CHO + Me-CHO - H2O -> Ph-CH=CH-CHO
This reaction can also be used for the preparation of homologue substances (c):
NO2-Ph-CHO + Me-CHO - H2O -> NO2-Ph-CH=CH-CHO
Ph-CHO + Et-CHO - H2O -> Ph-CH=C(-Me)-CHO
Cinnamaldehyde is a transparant, aromatic smalling and volatile oil. It boils at 128-130°C under 20 mmHg and has a density of 1.050 (20°C). Cinnamaldehyde reacts with NH3 in an alcoholic solution to yield hydrocinnamide (Ph-CH=CH-CH)3N2.
(a) "Zimmtöls"... SWIM doesn't know how to translate this well ::) . "Zimmt" means "cinnamic", so SWIM thinks it should be something like cinnamic oil. A synonym (trade name) is Cassia oil (Cassiaöls).
(b) The books adds a remark here: the commercially available "Zimmtblätteröl" (cinnamic oil from leaves) from the Cinnamonium ceylonicum contains eugenol as main component.
(c) Miller, Kinkelin, Ber. 19, 525 (1886)
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And where the f*ck is that allyl thing you talked about :) ? There is a small, condensed but well written page on Rhodium's site: https://www.thevespiary.org/rhodium/Rhodium/chemistry/cinnamaldehyde.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/cinnamaldehyde.html)
Don't know if you really want to go to the safrol if you can go to isosafrol as well using Perkin, but it could be usefull if you have problems or low yields with piperonal -> isosafrol. Safrol -> isosafrol is discussed ad nauseam on Rhodium and the Hive ;) .
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