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Organic Lab Reactions 107

Organic Lab Reactions 107 - 102 THE CANNIZZARO REACTION of...

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102 THE CANNIZZARO REACTION of the lime required in the above equation generally is used, 48 ' 49 > 60 although less than the stoichiometric amount of the base has been recommended in at least one instance. 61 The use of promoters such as copper oxalate, 62 formamide, 62 and sugars M has been described, as has also the use of quaternary ammonium bases. 44 The preparation of pentaerythritol in 56% yield on a laboratory scale has been described in Organic Syntheses.* 6 ' iS The modified procedure of Friederich and Brunn 47 gives better yields and is described in the experimental part (p. 111). Propionaldehyde 65 and isovaleraldehyde 66 have been converted to the corresponding trimethylol derivatives, CH 3 C(OH 2 OH) 3 and (CH3)2CHC(CH 2 OH) 3 , by treatment with formalin and calcium hydrox- ide; although the yields are not specified they appear to be good. Phen- ylacetaldehyde 66 did not give the expected product. The only useful Cannizzaro reactions involving the use of aldehydes
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