Water → 11-Methoxyundec-1-ene

Temperature

50 °C

Under an argon atmosphere a stirred mixture of 15.5 grams (0.375 mole) of sodium hydride (60% in mineral oil) in 180 ml of tetrahydrofuran was warmed to 50° C., and 28 ml (0.45 mole) of iodomethane was added portionwise. Upon completion of addition, 41.1 grams (0.24 mole) of 10-undecen-1-ol in 75 ml of tetrahydrofuran was added dropwise during a one hour period. Upon completion of addition, the reaction mixture was heated at 50° C. for an additional 90 minutes, and then it was allowed to cool to ambient temperature where it stirred for 60 hours. The reaction mixture was cooled in an ice water bath, and cold water was added dropwise until all of the solid material in the reaction mixture was dissolved. The aqueous layer was extracted with two portions of diethyl ether, and the ether extracts were combined with the organic layer from the reaction mixture. The organic layer extract combination was washed in turn with 50 ml of water and 50 ml of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated at atmospheric pressure to a residue. The residue was distilled under reduced pressure, yielding 36.1 grams of methyl 10-undecenyl ether; b.p. 99°-100° C./5.5 mm.

1. additionwas added dropwise during a one hour period
2. additionUpon completion of addition
3. temperaturethe reaction mixture was heated at 50° C. for an additional 90 minutes
4. temperatureto cool to ambient temperature where it
5. temperatureThe reaction mixture was cooled in an ice water bath
6. dissolutionwas dissolved
7. extractionThe aqueous layer was extracted with two portions of diethyl ether
8. extractionThe organic layer extract combination
9. washwas washed in turn with 50 ml of water and 50 ml of an aqueous solution saturated with sodium chloride
10. dry with materialThe organic layer was dried with sodium sulfate
11. filtrationfiltered
12. concentrationThe filtrate was concentrated at atmospheric pressure to a residue
13. distillationThe residue was distilled under reduced pressure

ORD record

ord-4c508102a318432cb0d9d3dc599576c9

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05081287