Oxidative Esterification of Aromatic Aldehydes Using Polymer-Supported Green Bromine

Abstract

A facile one-pot green chemical conversion of aromatic aldehydes to alkyl esters is described using polymer-supported bromine chloride resin in the presence of potassium carbonate at room temperature. This eco-friendly methodology with simple workup procedure and recovery and recyclability of the resin makes the transformation simple and efficient.

Key words

bromine chloride resin - esterification - oxidation - aldehyde - hypobromite ion

• References and Notes

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• 20 General Procedure for the Oxidation A mixture of bromine chloride resin and K₂CO₃ in MeOH–H₂O (8:2) 3 mL was placed in a round-bottom flask fitted with a magnetic stirrer. To this, the aldehyde (1 mmol, 1 equiv) was added dropwise, and the reaction mixture stirred at r.t. The progress of the reaction was monitored by TLC. After completion of the reaction the mixture was filtered, and the filtrate was extracted with Et₂O. The ether layer was washed with H₂O, brine, dried over Na₂SO₄, filtered, and concentrated. The residue was purified by column chromatography, if required, over silica gel (60–120 mesh) using a mixture of PE and EtOAc (9:1) as eluent.
• 21 Procedure for the Preparation of Bromine Chloride Resin A solution of 0.1 M KBr–KBrO₃ (20 mL) was added to a flask. Oven-dried Amberlite IRA-400 chloride resin (10 g) was added to the flask followed by 5 mL of HCl–H₂O (1:1). The solution was stirred for 5 min. The resin was filtered and washed with H₂O and dried.