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

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.

1. temperatureThe solution is cooled
2. extractionextracted with ether (3× 200 ml.)
3. dry with materialThe ethereal solution is dried (MgSO4)
4. filtrationfiltered
5. customthe ether evaporated
6. customto give
7. customrecovered
8. concentrationThe aqueous layer is concentrated to a small volume
9. customprecipitated salt
10. customis removed by filtration
11. washwashed with ether
12. extractionThe filtrate is extracted with ether (3× 100 ml.)
13. washthe combined extracts and ethereal wash
14. dry with materialare dried (MgSO4)
15. filtrationfiltered
16. customthe ether evaporated

ORD record

ord-571aac14335f470991804832d0135594

Source dataset

uspto-grants-1977_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04029786