hi, bees.
here's the catch: i'm in search of a practical otc and large scale
propenylbenzene to benzaldehyde oxidation. with large scale i mean
something like 50-100g per batch. if you think i demand too much,
please note that yields don't need to be high. 50% is perfectly ok,
30% (reproducible) is acceptable. the propenylbenzene at hand is
anethole, but i'm not pissed if it works on other substrates
.
i've found the following oxidation methods, but they all suck:
a) old-school KMnO4: this needs huge amounts of solvent, gives
low inconsistent yields, ugly sideproducts and just sucks.
b) KMnO4 on solid support: this can give nice yields, but the amount
of oxidation agent is just ridiculous.
c) electrolysis: the paper i have gives low (but acceptable) yields
due to overoxidation, is slow and needs _lots_ of current. i'm not
going to pump several ampere for several days through my solution.
and the needed equipment is rather expensive/hard to make.
d) dichromate, CrO3 and similar: not otc
e) weird Ru or other complexes: not otc
f) ozonolysis: working with gases sucks. you don't know how much was
produced, how much was taken up, you have to somehow dispose of your
toxic gases, the ozone generator is either expensive or of unknown quality.
in short: a questionable investment
g) CuO (as in
Post 293365
(Antoncho: "Double bond ox. cleavage (to aldehyde) with CuO", Chemistry Discourse)):
i guess this won't work, since anethole does not dissolve in water.
i'd be very grateful for any hints/ideas.
otherwise i'm stuck with a) and f), a) sucking ass and f) maybe not
even being a possiblity