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Topic: Catalytic hydrogenation of benzyl ester  (Read 2259 times)

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Offline Martin4

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Catalytic hydrogenation of benzyl ester
« on: March 25, 2016, 02:15:02 PM »
I need a mechanism for hydrogenation of benzyl ester with Pd/C as catalyst. The reaction is performed at room temperature for 1h under pressure of H2, p=50 psi. Catalyst as a precipitate needs to be removed and washed with MeOH/H2O (1/1). I suppose a insertion of palladium occur, oxidative addition, and Pd is oxidized to Pd(II), and then a H2 is coordinated to Pd(II). The products are toluene and carboxylic acid. This is the reaction:

« Last Edit: March 25, 2016, 02:57:51 PM by Martin4 »

Offline TheUnassuming

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Re: Catalytic hydrogenation of benzyl ester
« Reply #1 on: March 25, 2016, 03:02:16 PM »
Your proposed mechanism is correct as far as I know.
When in doubt, avoid the Stille coupling.

Offline AWK

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Re: Catalytic hydrogenation of benzyl ester
« Reply #2 on: March 25, 2016, 03:42:10 PM »
google for details

H2 Pd/C Mechanism for Benzyl Deprotection
AWK

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