Hydrochloric Acid → 4-Benzyl-3-methyl-5-oxomorpholine-3-carboxylic acid

Participants

Reaction Steps

Combine 4-benzyl-5-(hydroxymethyl)-5-methylmorpholin-3-one (11.75 g, 0.05 mol) ethyl acetate (75 ml), and KBr in water (0.5 M, 10 ml), followed by addition of 2,2,6,6-tetramethylpiperidine-1-oxyl (0.16 g, 1 mmol). Add solution of 12% NaClO in water (39 g, 62.5 mmol) dropwise to the mixture over 30 minutes at 5° C. at pH of 8.0-10.0. After 30 minutes, adjust the pH to 5.0 by addition of 35% hydrochloric acid, followed by addition of 25% NaClO2 in water (22.7 g, 62.5 mmol) over 30 minutes. Stirring continues for 3 hours at ambient temperature. Recover the product by extraction with ethyl acetate, washed with brine, to give 4-benzyl-3-methyl-5-oxomorpholine-3-carboxylic acid.

Provenance & Evidence