Catalytic hydrogenation Catechol derivatives

Catechol is an intermediate for the synthesis of racemic adrenaline which, although quite medicinally active, can be resolved (ref. 36) in 71% yield to afford the more active R(-) enantiomer, the natural form, which can also be derived quantitatively by asymmetric reduction (ref. 37) of the synthetic precursor, adrenalone as the hydrochloride by catalytic hydrogenation in methanol containing the rhodium complex of (R)-o[(S)-1 ,2-bis(diphenylphosphine)ferrocenyl]ethyl alcohol. Adrenalone is obtained by the acylation of catechol with chloroacetyl chloride to afford 3,4-dihydroxy-w-chloroacetophenone followed by reaction with methylamine. 

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