1-Hexadecanol, 1-(4-methylbenzenesulfonate) → Hexadecylphosphonic Acid

To ethyl phosphite (1.6 g) dissolved in 5 ml of tetrahydrofuran was added sodium (180 mg), and the mixture was dissolved. To this solution was added cetyl tosylate (514 mg), and the mixture was refluxed for ten hours. The reaction solution was concentrated to dryness under reduced pressure. To the residue was added water, which was acidified with concentrated hydrochloric acid, followed by extraction with ether and dried on Na2SO4. From the extract was removed the solvent by evaporation, and the residue was subjected to a silica-gel (7 g) chromatography. Fractions eluted with chloroform were collected and concentrated to dryness. To the residue was added concentrated hydrochloric acid (3 ml), which was refluxed for 18 hours. The resulting precipitates were collected by filtration, followed by recrystallization from n-hexane to give 240 mg (60%) of colorless needles.

1. dissolutionthe mixture was dissolved
2. temperaturethe mixture was refluxed for ten hours
3. concentrationThe reaction solution was concentrated to dryness under reduced pressure
4. additionTo the residue was added water, which
5. extractionfollowed by extraction with ether
6. customdried on Na2SO4
7. customFrom the extract was removed the solvent
8. customby evaporation
9. washFractions eluted with chloroform
10. customwere collected
11. concentrationconcentrated to dryness
12. additionTo the residue was added concentrated hydrochloric acid (3 ml), which
13. temperaturewas refluxed for 18 hours
14. customThe resulting precipitates
15. filtrationwere collected by filtration
16. customfollowed by recrystallization from n-hexane

ORD record

ord-d9ab60f16bf749a385830ad22f7e897f

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04935520