plutonium243 - 26-1-2023 at 17:31
I'm looking for an alternative, and Ideally more common, high temperature solvent to use for the catalytic synthesis of allylaromatic hydrocarbons. In
the paper I read (DOI: 10.1007/BF00845602), they added the hydrocarbon (say toluene or benzene) and catalyst of zinc chloride to a solution of allyl
alcohol and either n-nonane or n-undecane, and then boiled until completion at ~108-120° C. Due to the high boiling point of toluene, they managed to
run it solvent free, however all of their runs required undecane for the benzene version. I looked around, and it seems that undecane is somewhat rare
and rather pricy. Can anyone think of a more common (and ideally less expensive) solvent that can be used. I was thinking using something like DMSO,
as it seems to be miscible with benzene, dissolve both allyl alcohol and zinc chloride, and has a boiling point well above what is required. Does
anyone know if there is any problems in using it? Alternatively, dodecane was more accessible, although still quite far from ideal. I would assume
that there should be no problems with it instead, right?
Any suggestions would be much appreciated.
DraconicAcid - 26-1-2023 at 17:48
If you use an alkyl halide instead of an alcohol, you can often get away with dichloromethane and FeCl3.
plutonium243 - 27-1-2023 at 08:27
Wait, an alkyl halide and not an allyl halide? I would think that something like, say, propyl chloride would react to produce propyl or isopropyl
benzene rather than allylbenzene. Also do the chlorides work well, since they seem more common than the bromides?
DraconicAcid - 27-1-2023 at 09:33
I use t-butyl chloride/FeCl3 in dichloromethane. Allyl chloride would probably work just as well because allyl cations are resonance stabilized. A
secondary or primary alkyl chloride would probably not work as well (but I haven't tried them).