Reaction #2006438

Reaction equation

n-butyllithium

methacryloyl chloride

sodium bicarbonate

1-ethyl-1-cyclooctanol

→

title compound

Yield 51.0%

1-Ethylcyclooctyl Methacrylate

Yield 51.0%

Solvents

diethyl ether

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   OtherTo a 500-mL 3-necked round bottom flask equipped with a 250-mL pressure
2. 2
   workup.ADDITIONaddition funnel, a nitrogen inlet with thermocouple and an overhead stirrer
3. 3
   workup.ADDITIONwas then added slowly
4. 4
   Temperaturewith cooling over 1.5 hours
5. 5
   workup.ADDITIONwas carefully added
6. 6
   workup.STIRRINGThe mixture was stirred for 1 hour at which time it
7. 7
   Washthe organics washed with water, brine
8. 8
   Dryingdried for 1 hour over anhydrous magnesium sulfate
9. 9
   FiltrationFiltration and removal of the solvent at reduced pressure
10. 10
    Otherresulted in a light-colored oil which
11. 11
    workup.DISTILLATIONwas distilled twice from Na2CO3 and phenothiazine through a based-washed 15-cm Vigreux

Procedure

To a 500-mL 3-necked round bottom flask equipped with a 250-mL pressure equalizing addition funnel, a nitrogen inlet with thermocouple and an overhead stirrer was added 32.5 g (0.208 mol) of 1-ethyl-1-cyclooctanol and 100 mL of anhydrous tetrahydrofuran. The addition funnel was charged with 150 mL (0.239 mol, 15% excess) of n-butyllithium (1.6M in hexane) which was then added to the cooled alcohol over 2 hours. The addition funnel was then charged with a solution of 25 g (0.239 mol) of freshly distilled methacryloyl chloride in 50 mL of dry tetrahydrofuran which was then added slowly with cooling over 1.5 hours. The reaction mixture was allowed to warm to room temperature with stirring overnight after which 100 mL of saturated sodium bicarbonate was carefully added with stirring. The mixture was stirred for 1 hour at which time it was diluted with 500 mL of diethyl ether and the organics washed with water, brine and dried for 1 hour over anhydrous magnesium sulfate. Filtration and removal of the solvent at reduced pressure resulted in a light-colored oil which was distilled twice from Na2CO3 and phenothiazine through a based-washed 15-cm Vigreux to yield 24 g (51%) of the title compound (bp 84° C.@ 1 mmHg) as a clear, colorless oil.

Source