[limonade]

Can I do a side chain oxidation toulene with H2CrO4 and heat  or is this only possible with KMnO4?

I'm trying to do the reaction in the picture. Ignore the number 2.

[Hunter2]

Yes it is possible.

http://www.mhhe.com/physsci/chemistry/carey/student/olc/ch19preparecarboxylic.html#benzenes

[Archer]

I am quite nervous of chromic acid as an oxidising reagent as it can react explosively with certain organic substances.

I have used it a number of times, successfully, to make ketones from alcohols but it is always carried out at room temp with external cooling where necessary.

Chromic acid is used as a cleaning solution in some labs and serious explosions have resulted from heating the mixture to try to remove stubborn residues.

Make sure if you are going to attempt this that you find a procedure for doing it, don't just "see if it works" or you could seriously injure yourself and / or others.

[Hunter2]

Additionally I would avoid to work with it at all, because Chromium-Vi compounds strong poison and also carcinogen.

[orgo814]

If this is a homework problem, then yes that's fine. If you're trying to do this in the lab, like the others said, it would work but it's more dangerous and a lot more expensive if I may add. Also, the atom economy is not as good if we bring green chemistry into this.