convert benzene into m nitro chloride Benzene
Answers
This is a little trickier than you might think at first glance. One approach is to nitrate benzene to nitrobenzene and then a Friedel-Crafts reaction with methyl chloride/AlCl3. The nitro group is a meta director but it is also a strongly deactivating group toward electrophilic aromatic substitution and, consequently, the Friedel-Crafts reaction will fail.
So, it looks like a more involved route may be necessary. The approach could be to 1) methylate with CH3Cl/AlCl3 to give toluene, 2) Nitrate with HNO3/H2SO4 to give mainly p-nitrotoluene. 3) Reduce the nitro to an amino group (Sn/HCl). 4) Acetylate the amino group (Acetyl-Chloride/base). Now you have an o/p-director para to the methyl group. So, 5) nitrate again, 6) hydrolyze the acetyl group off, 7) diazotize the resulting amine with nitrous acid, and 8) let it decompose in ethanol. OK, a lot of steps. The scheme below shows these steps.
This is a little trickier than you might think at first glance. One approach is to nitrate benzene to nitrobenzene and then a Friedel-Crafts reaction with methyl chloride/AlCl3. The nitro group is a meta director but it is also a strongly deactivating group toward electrophilic aromatic substitution and, consequently, the Friedel-Crafts reaction will fail.
So, it looks like a more involved route may be necessary. The approach could be to 1) methylate with CH3Cl/AlCl3 to give toluene, 2) Nitrate with HNO3/H2SO4 to give mainly p-nitrotoluene. 3) Reduce the nitro to an amino group (Sn/HCl). 4) Acetylate the amino group (Acetyl-Chloride/base). Now you have an o/p-director para to the methyl group. So, 5) nitrate again, 6) hydrolyze the acetyl group off, 7) diazotize the resulting amine with nitrous acid, and 8) let it decompose in ethanol. OK, a lot of steps. The scheme below shows these steps.
OK, this route will get you to where you want to go but it is a lot of steps (8) and even if you are lucky and every step, after isolation, is an 80% yield reaction, the overall yield will be ~17%. Something a little faster would be better. An option that is only three steps is shown below. The steps would be 1) Freidel-Crafts with CO/AlCl3/HCl to give benzaldehyde. The -CHO group is a meta director so 2) nitrate to give m-nitrobenzaldehyde. Finally, 3) a Wolff-Kishner reaction to reduce the aldehyde to a methyl group.