[asd34]

Can someone tell me that, the posted synthesis way is possible on paper? Or give a little help for a different way, which possibly works good in lab:)

[Hunter2]

Probably yes, but not in one pot.

[discodermolide]

I think the benzyl alcohol is a bit sterically hindered for it to react with phthalic anhydride. I seem to remember that you can buy the mono-acid chloride-mono methylester of phthalic acid from Aldrich? That would be more reactive.

methyl 2-(chlorocarbonyl)benzoate

Then you would need to remove the other ester.

[orgopete]

Probably yes, but not in one pot.

This comment is prescient here as the reactions are incomplete. Only the Grignard reaction is the solvent listed. No workup of the Friedel-Crafts acylation is given and no proton source for its reaction with the Grignard.

Disco's comment is a good one, though I don't think the person designing the problem anticipated a solution so difficult. None the less, the acylation needs a catalyst to proceed. I think steric hindrance will affect the rate more than the equilibrium. Phthalic acid mono-t-butyl ester has been reported, so I expect the reaction should succeed, but probably not without a catalyst.

[asd34]

Thank you for the answers!