Allyl chloride → 1-Propene, 3-[2-(2-methoxyethoxy)ethoxy]-

Temperature

10 °C

1,700 mls of dried peroxide free tetrahydrofuran, available from Fisher Scientific Company, 15 Jet View Drive, P.O. Box 8740, Rochester, NY 14624 and 158.7 g potassium metal, available from Fisher Scientific, are charged under dry nitrogen into a 5,000 ml three-neck round bottom flask equipped with mechanical stirrer. The solution is chilled to 10° C., using an icewater bath and 494 ml of diethylene glycol monomethyl ether, available from Chemical Samples Company, 4692 Kenny Road, Columbus, OH 43221, is added dropwise. The potassium metal reacts within 24 hours at which time 350 mls of allyl chloride available from Aldrich, 159 Forest Street, Metuchen, NJ 08840, is added dropwise at such a rate to maintain a gentle reflux. After the reaction is allowed to continue overnight, one liter of distilled water is added to the reaction vessel to dissolve the precipitated salts. The tetrahydrofuran layer is washed three times with a salt water solution (270 g NaCl to 1 liter H2O) to remove excess alcohol. The tetrahydrofuran is removed with a water aspirator and the product is distilled at reduced pressure. 410 g of diethylene glycol allyl methyl ether is obtained (b.p. 109° C./30 mm). The analytical data is consistent with a product of the general formula:

1. customequipped with mechanical stirrer
2. additionis added dropwise at such a rate
3. temperatureto maintain a gentle reflux
4. dissolutionto dissolve the precipitated salts
5. washThe tetrahydrofuran layer is washed three times with a salt water solution (270 g NaCl to 1 liter H2O)
6. customto remove excess alcohol
7. customThe tetrahydrofuran is removed with a water aspirator
8. distillationthe product is distilled at reduced pressure

ORD record

ord-8db5359f418749dd8ea13654a08a2265

Source dataset

uspto-grants-1981_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04259467