So, How would you oxidatively cleave the terminal olefin in 2-allylphenol to give 2-hydroxyl-phenylacetic acid.
Because heres what does not work:
KMnO4 in 1M Sulfuric acid, Nope.
Ozonolysis is MeOH followed by hydrogen peroxide, Nope.
I am trying this right now: JACS 2002, 124, 3824. 0.01 eq potassium osmate, 4.0 eq oxone, done at 0.2 M in DMF. Reaction is done at RT and ref gave now indication of an exothermic reaction....well it was.
My issue is the phenol. I am oxidizing to the quinone, at least with KMnO4 I did. Do we think I should just protect or do you fine chemists have another recommendation?
I was thinking Lemieux-Johnson followed by Pinnick to give acid if I really do not want to protect.