Isopropanol → 2-(Ethylbutoxyphosphinyl)acetic acid

Participants

Reaction Steps

19.4 g (0.1 mol) of butyl ethyl(2-hydroxyethyl)phosphinate (prepared as in Example 6) in 500 ml of acetone were admixed with 0.11 mol of Jones reagent (12.7 g of chromium trioxide in 36.7 ml of water and 11.0 ml of concentrated sulfuric acid) at 0° C. by dropwise addition. The reaction mixture was subsequently stirred for 3½ hours with ice cooling and for 1 hour at room temperature. Following addition of 12 ml of isopropanol, the mixture is poured onto ice-water. Volatile constituents are then distilled off in vacuo. The residue was taken up in tetrahydrofuran and extracted. Insoluble salts were filtered off. The solvent of the filtrate was removed in vacuo and the residue was recrystallized from acetone to obtain 1.68 g (81% of theory) of 2-(ethylbutoxyphosphinyl)acetic acid as colorless solid.

Provenance & Evidence