A new method for the hydroxymethylation of carbonyl compounds

✍ Scribed by Tsuneo Imamoto; Toshiaki Takeyama; Masataka Yokoyama

• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 128 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)91015-9

✦ Synopsis

Benzyl chloromethyl ether reacts with carbonyl compounds in the presence of Sm12 to afford alcohols (I), which are subsequently subjected to hydrogenolysis to yield diols (II).

The nucleophilic hydroxymethylation is of potential utility in synthetic organic chemistry and several methods have been devised, particularly for the substitution of halogen atom of vinylic or alkyl halides for hydroxymethyl group. 1) However, the hydroxymethylation of carbonyl group has only been described in a few papers. 2,3) We report herein a new approach for the hydroxymethylation of carbonyl compounds. The overall sequence is shown as follows: