Hi,
i didn't find many posts on the RITTER reaction (R-CN with tertiaries alcohols for example PCOH phenyl-1-cyclohexanol, to get a primary amine, through a way that avoids the deshydratation reaction that would happen by reacting tertiary halide with primary amine, or hexamine)
the nitrile: NaCN can be used too, Ph-CN, Et-CN
the alcohol must be acidified to get the "free" carbocation...
H2SO4 can be used for it..
I guess all strong acids can ?
do the yields depend of the nitrile used ?
but my biggest problem is not the yields:
NaCN + strong concentrated acid --> free HCN gaz
NaCN + diluted strong acid --> H+ CN-
same with R-CN...
proposed method:
0.1mol R3-OH is mixed with water and polar organic solvent
(ether, toluene?) and 0.15 mol H2SO4
THEN organic phase is separated
and reacted with 0.1mol R-CN or NaCN
finally the amide is hydrolized and no free HCN, no CN- has been formed at all...
will the alcohol sulfuric ester be formed or will the alkene be formed by deshydratation?
will the organic phase separation work? will the acidified alcohol leave the water phase?
tks for your comments