N-Formylmorpholine → Morpholinium, 4-(chloromethylene)-, chloride

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Reaction Steps

Under dry nitrogen, a solution of N-formyl morpholine (50.6 gm) 440 mmol) in anhydrous diethyl ether (300 ml), stirring rapidly in an ice bath is treated dropwise with a solution of oxalyl chloride (50.8 gm, 400 mmol) in hexane (30 ml). After warming to room temperature for 30 minutes, the solid product is filtered off under dry nitrogen and dried in vacuum to give 91.5% (62.2 gm, 366 mmol) of N-(chloromethylene)-morpholinium chloride.

Provenance & Evidence