What if a bee has certain phenolic carboxylic acids, like say: 3,4,5-trihydroxy-benzoic acid, 3,4-dihydroxy-benzoic acid, and 2,5-dihydroxy-benzoic acid, and this bee wants to alkylate those phenolic hydroxies, but wants to protect the carboxylic acid?
How do you solve this issue? Is there either a way to selectively alkylate the hydroxies, or can one just alkylate the fuck out of the molecule, then hydrolyze the alkyl ester produced of the carboxylic acid with alakai? Would this hydrolyze the phenol esters too?
Essentially SWIPP wants to: Ph(OH)x(COOH) --> Ph(OR)x(COOH) or Ph(OR)x(COOR) --> Ph(OR)x(COOH)
How can an evil bee chemist accomplish this? Anything special to it, or just alkylate like normal, and hydrolyze with KOH?
Thank you in advance guys. I appreciate your help and advice as always.
PrimoPyro
Vivent Longtemps la Ruche!