Sodium Hydroxide → 2-Hydroxymethyl-4-n-propylmorpholine

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Reaction Steps

2-Allyloxymethyl-4-n-propylmorpholine (59.7 g.) is heated under reflux in hydrochloric acid (240 ml.; 20% ) for 18 hours. The solution is cooled, diluted with ice and water, basified with sodium hydroxide and extracted with ether (3× 200 ml.). The ethereal solution is dried (MgSO4), filtered and the ether evaporated to give recovered starting material. The aqueous layer is concentrated to a small volume and precipitated salt is removed by filtration and washed with ether. The filtrate is extracted with ether (3× 100 ml.) and the combined extracts and ethereal wash are dried (MgSO4), filtered and the ether evaporated. 2-Hydroxymethyl-4-n-propylmorpholine (16.7 g.) is obtained as a viscous oil which forms a hydrogen oxalate, m.p. 133°-135° C. after crystallisation from a methanol/ether mixture.

Provenance & Evidence