Esterification of Aldehydes and Alcohols with Pyridinium Hydrobromide Perbromide in Water

Abstract

The direct esterification of aldehydes and alcohols was carried out with pyridinium hydrobromide perbromide in water at room temperature. A variety of aldehydes were converted to respective ester derivatives with alcohols such as methanol, 1,2-ethanediol, 1,3-propanediol. Further, a variety of aliphatic alcohols were also converted to the corresponding Tishchenko-like dimeric esters in good yields under the same reaction conditions.

esterification - water - pyridinium hydrobromide perbromide - aldehyde - alcohol

References

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Typical Procedure for the Dimeric Esterification of Dodecanol ( 12): To a solution of PHPB (160 mg, 0.50 mmol) in H₂O (8 mL) was added 12 (46 mg, 0.25 mmol). After stirring for 13 h at r.t., the reaction mixture was treated with 0.5 M aq Na₂S₂O₃ and extracted with EtOAc. The organic layer was washed with 0.5 M aq Na₂S₂O₃, successively sat. aq NaCl, and_dried over MgSO₄. After removal of the solvent in vacuo, the residue was purified by column chromatography on silica gel (Wakogel C-200) with CCl₄. Dimeric ester 12a (44 mg, 0.12 mmol) was obtained in 95% yield.