[benjaminchea]

Hydrolysis of methyl salicylate gives an intermediate salt that is acidified to a carboxylic product, salicylic acid. Hydroxytoluene is a benzene ring with substituents of a methyl group and a hydroxyl group. One method that seems plausible is to use an oxidizing agent such as potassium manganate and convert the side chain to a carboxylic acid. Is this another correct way to synthesize salicylic acid starting from o-hydroxyltoluene? Please explain if necessary and provide a mechanism (complicated) if you can. I thank you ahead of times.

Edit: how to synthesize salicylic acid from o-cresol is the general question. Please help.

[HP]

Its possible to obtain your product by first halogenation ArCH3 group with Cl2 to mono or dichloro aducts but as having OH phenolic group then its possible such reaction to lead also to Ar-halogenation...If not so then:
Ar-CH3 + Cl2 --> Ar-CH2Cl (as o-hidroxy benzyl chloride 
The using Sommelet reaction with hexamethylenetetramine (urotropin) at heating which should lead to salycilic aldehyde:
Ar-CH2Cl + C6H12N4 + H2O -->Ar-CHO
Y
then you may easili oxidize salycilic aldehyde to salycilic acid with some weak oxidizing agent or with air and some salt catalyst..
From dihalo product:
Ar-CHCl2 + NaOH/H2O --> ArCHO and so on...
Of course classic Colbe method starting simply from Na-phenolate and CO2 to salycilic acid is most practically efficient i think.

[jwesterway]

not sure of the yields but it would be fairly simple to esterify the OH to form the ester with formic or acetic acid then oxid the product with permanganate to convert the methyl into the carboxylic acid and finally hydrolysis of the ester to recover the OH group, this would leave you with your desired product.

Isn't this what you were looking for?

-Josh