Diethyl Ether → HCID 22632112, compound

Participants

Reaction Steps

4-Bromomethylbenzoic acid (50 g, 233 mmol) is dissolved in 500 mL of tetrahydrofuran containing a few drops if N,N-dimethylformamide at room temperature under nitrogen and treated dropwise over 1 hour with oxalyl chloride (268 mmol, 34.0 g, 23.4 mL). After the addition, the reaction mixture is stirred for 0.5 hour, at which point the solvent is removed in vacuo. The solid residue is dissolved in 200 mL of tetrahydrofuran and poured into a rapidly stirring solution of diethylamine (536 mmol, 39.2 g, 55.7 mL) in 400 mL of water. After the mixture cools to room temperature, 100 mL of ether are added and the two phases are separated. The organic phase is dried over magnesium sulfate and concentrated in vacuo affording 54.01 g (200 mmol, 86% yield) of the product as a white solid.

Provenance & Evidence