N,N,N',N'-Tetramethylmethanediamine → 5-((Dimethylamino)methyl)-2-furanmethanol

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In a series of experiments with 2-furanmethanol we have found that the use of bis(dimethylamino)methane gives better yields of 5-(dimethylaminomethyl)-2-furanmethanol than those obtained using dimethylamine and a source of formaldehyde (e.g. aqueous formaldehyde, paraformaldehyde and trioxan). Furthermore the product obtained after distillation was also purer. The yields referred to above were 76-94% and these compare very favourably with the yields reported by R. F. Holdren (12%) (J. Amer. Chem. Soc. 69(464)1947) and Gill and Ing (70%) (J. Chem. Soc. 4728 (1958)).

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