Béhal-Sommelet rearrangement

What is Béhal-Sommelet rearrangement?

The Béhal-Sommelet rearrangement was originally reported by Béhal and Sommelet in 1904. This transformation involves the conversion of methyl β-hydroxylalkyl ethers into aldehydes when exposed to acids, preferably oxalic acid.

Béhal-Sommelet rearrangement
Béhal-Sommelet rearrangement
  • R1 = alkyl, aryl
  • R2 = Me, Et
  • R3 = alkyl, aryl

The methyl β-hydroxylalkyl ethers can be obtained through the Grignard Reaction of esters of α-methoxy acetic acids. This method is commonly used for producing α-branched aldehydes.

References

Béhal M. M. A. and Sommelet M., Bull. Soc. Chim. Fr., 1904, 31, 300

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