Aromatic Ester Hydrogenation --> Aromatic Ether?

[PrimoPyro]

Can you use catalytic hydrogenation to reduce an ester of a carboxylic acid and a phenol to an alkyl ether?

Like say reducing phenyl acetate to ethoxybenzene, or even more applicable, phenyl formate to methoxybenzene.

If one had a 2,5-dihydroxy-nitrostyrene he wanted to play with, could he form the diformate diester on the hydroxies, and catalytically hydrogenate the fuck out of the molecule to reduce both formyl groups and the nitroalkene to 2,5-dimethoxy-phenethylamine?

Just wondering, thanks.....

                                                   PrimoPyro
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[Rhodium]

The intermediate between a phenyl formate and a methoxybenzene is the phenolic hemiacetal of formaldehyde. I would expect that to hydrolyze too fast for an ether to form.

[PrimoPyro]

Yeah, me too, now that you put it that way.

Damn, and I thought I had found a cool shortcut.  

Im really getting interested in the possibility of CTH with Urushibara Nickel. You know I didn't know wtf CTH was until a few people started talking about it in threads recently, and I was like wtf? So I searched for it on your website, and behold, know I have learned something wonderful that I didn't know about before.  

                                                   PrimoPyro
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