Phenol from Toluene

[itslenders]

I am not sure if this is a stupid question (I did a search and found nothing) but is it possible to convert Toluene to Phenol by any simple method?

Toluene is easy to come by (even available at hardware stores) but Phenol is very difficult and expensive to get.

[megalomania]

That depends on what your definition of simple is. It is not that difficult to oxidize toluene to benzoic acid using potassium permanganate among many other oxidizing reagents; a procedure I believe is on my website.

The benzoic acid then undergoes further oxidation to phenol. Molten benzoic acid and catalytic amounts of magnesium benzoate and cupric benzoate (formed by reacting copper oxide and magnesium oxide with benzoic acid) are sparged with air and steam. Phenol then distills off.

For more specifics on the latter process see US patent 3,929,911, and for a less efficient, but lab scale reaction see US patent 2,762,838.

There are other ways, but that is the top method using toluene as a starting material.