Allyl Alcohol → 2-propenyl trimethylacetate

A stirred solution of 11.6 grams (0.20 mole) of 2-propen-1ol in 100 ml of pyridine was heated to reflux. To this was added dropwise 24.1 grams (0.02 mole) of trimethylacetyl chloride. The exothermic reaction caused the reaction mixture temperature to become excessive. The heat source was removed, and the reaction mixture was cooled in an ice bath. The addition of the acid chloride was continued to completion. Upon completion of addition, the reaction mixture was warmed to reflux where it stirred for one hour. After this time the reaction mixture was cooled to ambient temperature where it stood for 60 hours. The reaction mixture was shaken with 700 ml of water, and the organic layer was separated. The aqueous layer was washed with two 15o ml portions of diethyl ether. The washes and the organic layer were combined and washed with two 75 ml portions of an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. Low boiling volatile materials were removed from the oil by distillation under reduced pressure (b.p. 87°-100° C./21 mm), yielding 12.3 grams of 2-propenyl trimethylacetate as a residue. The nmr spectrum was consistent with the proposed structure.

1. customThe exothermic reaction
2. customThe heat source was removed
3. temperaturethe reaction mixture was cooled in an ice bath
4. additionThe addition of the acid chloride
5. additionUpon completion of addition
6. temperaturethe reaction mixture was warmed
7. temperatureto reflux where it
8. waitstood for 60 hours
9. stirringThe reaction mixture was shaken with 700 ml of water
10. customthe organic layer was separated
11. washThe aqueous layer was washed with two 15o ml portions of diethyl ether
12. washwashed with two 75 ml portions of an aqueous solution saturated with sodium chloride
13. dry with materialThe organic layer was dried with magnesium sulfate
14. filtrationfiltered
15. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
16. customwere removed from the oil by distillation under reduced pressure (b.p. 87°-100° C./21 mm)

ORD record

ord-d8a94d1aa500492baaf22bd14e48d6d4

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05081287