Question #b6c38

1 Answer
Jan 27, 2018

The classic way would be to make the tolyl sulfonate ester.....

Explanation:

And so....

#ROH + Cl(O=)_2SC_7H_8stackrel(H^+, C_6H_5N)rarrRO-S(=O)_2C_7H_8+HCl*NC_6H_5#....

The sulfonate is an excellent leaving group that can be displaced by moderate nucleophiles....

When you do these reactions, you will not be a popular man/women. Toluene sulfonyl chlorides have a powerful, penetrating smell of rancid butter...and even with a lot of care, and an efficient hood, your neighbours will come around acomplaining....and you also have to use pyridine...