Post 378325 (missing)
(fallen_Angel: "P2P - íîâàÿ èäåÿ.", Russian HyperLab)We to pulp carbide in a dust, we add benzyl chloride (or its solution?):
CaC2 + C6H5CH2Cl - > C6H5CH2C2CaCl
Then we add water, we receive 3-phenil-1-propyne..
Wouldn't the following side reaction be crippling to yields?
BzC2CaCl + BzCl ----> BzC2Bz + CaCl2
My idea was this: prepare a C2H- Ca salt via reaction of CaC2 with a dry liquid amine (such as diisopropylamine, which is easily prepared from ammonia, acetone, and Al/Hg amalgam).
As in:
CaC2 + R2NH ----> Ca(C2H)(R2N)
Amines are less acidic than the first hydrogen in acetylene, but (if I remember correctly) more acidic than the second.
And there we have it - our reagent for the nucleophilic substitution:
3BzCl + Ca(C2H)(R2N) ----> BzC2H + Bz2NR2Cl + CaCl2
Bull. Soc. Chim. France [5] 20, C46-C48 (1953) (https://www.thevespiary.org/rhodium/Rhodium/pdf/quelet.chloromethylation.pdf)
(https://www.thevespiary.org/rhodium/Rhodium/pdf/quelet.chloromethylation.pdf)Post 299551 (https://www.thevespiary.org/talk/index.php?topic=6905.msg29955100#msg29955100)
(karel: "Chloromethylation", Chemistry Discourse) Or your chloromethylation at room temperature gave only desired 4-bromo compound?