Sequential Rosenmund and Clemmensen Reductions of Acid Chloride

Rarely Tested

Carboxylic acids are not reduced directly to alkanes by Zn-Hg/HCl.


$$\lt br/\gt RCOOH \;\not\longrightarrow_{\mathrm{Zn\!-\!Hg}/\mathrm{HCl}}\; RCH_3\lt br/\gt $$

Instead, via acid chloride:

  • Rosenmund reduction:
    $$RCOCl \xrightarrow{\mathrm{Pd/BaSO_4},\,H_2} RCHO$$
  • Clemmensen reduction:
    $$RCHO \xrightarrow{\mathrm{Zn\!-\!Hg},\,\mathrm{HCl}} RCH_3$$
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