Hydrochloric Acid → 1-Chloro-3,6,9-trioxadecane

19.02 g (0.116 mol) of triethylene glycol monomethyl ether and 21 ml (20.54 g=0.26 mol) of pyridine in 110 ml of benzene are heated to reflux, and 19 ml (31 g=0.26 mol) of thionyl chloride are added dropwise thereto. The mixture is boiled under reflux for a further 20 hours. When the reaction solution has cooled, a mixture consisting of 5 ml of concentrated hydrochloric acid and 20 ml of water is added thereto, with stirring. The organic phase is separated off and washed repeatedly with water and brine. The solvent is extensively distilled off using a Vigreux column and the residue is purified on silica gel in hexane/ethyl acetate (4:1). The product-containing fractions are concentrated and the residue is distilled, yielding 3,6,9-trioxadecyl chloride (J. Am. Chem. Soc. 89, 7017 (1967)); b.p. 76° C./2 mbar, NMR (CDCl3): 3.8-3.5 (m,12H); 3.37 (s,3H).

1. temperatureto reflux
2. temperatureunder reflux for a further 20 hours
3. temperatureWhen the reaction solution has cooled
4. additionis added
5. customThe organic phase is separated off
6. washwashed repeatedly with water and brine
7. distillationThe solvent is extensively distilled off
8. customthe residue is purified on silica gel in hexane/ethyl acetate (4:1)
9. concentrationThe product-containing fractions are concentrated
10. distillationthe residue is distilled

ORD record

ord-98384c46def84a658377525bdd0573cd

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05686439