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Organic Lab Reactions 184

Organic Lab Reactions 184 - INTRODUCTION 179 PAGE Reduction...

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INTRODUCTION - 179 PAGE Reduction of Ketones ' 202 Procedure IV (For Ketones Boiling aSbve 175-200°) 203 Reduction of Benzophenone '. 203 Procedure V (For Ketones Resistant to Reduction) 204 Reduction of 4-Keto-l,-2,3,4-tetrahydrochrysene in Toluene 204 Reduction of Acetals or Enol Ethers 204 StFBVEY or ALUMINUM ALKOXIHE REDUCTIONS REPORTED IN THE LITERATURE . 205 Table I. Reduction of Aldehydes with Aluminum Alkoxides 206 Table II. Reduction of Ketones with Aluminum Isopropoxide , 209 INTRODUCTION In 1925 it was discovered independently by Verley x and by Meerwein and Schmidt 2 that an aldehyde can be reduced to the primary alcohol by treatment with aluminum ethoxide in the presence of ethanol. The reduction of the aldehyde occurs at the expense of an equivalent amount of ethanol which is oxidized to acetaldehyde. A K O C J H J ) , RCHO + CH 8 CH 2 OH ( > RCH 2 0H -f- CH S CHO The reaction is reversible, but the equilibrium can be shifted to the point of complete reduction by removal of the acetaldehyde with a stream of dry hydrogen or nitrogen.
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