Methacryloyl chloride → HCID 57528149, compound

HRID 1453526Notes

Reaction equation

HRID 1453526 reaction equation
[CH2:1]([C:3]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:2].C([Li])CCC.[C:17](Cl)(=[O:21])[C:18]([CH3:20])=[CH2:19].C(=O)(O)[O-].[Na+]>O1CCCC1.C(OCC)C>[C:17]([O:11][C:3]1([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)(=[O:21])[C:18]([CH3:20])=[CH2:19]

Participants

7

Reactant 4

HCID 13528Methacryloyl chlorideHCID 516892Sodium BicarbonateHCID 19931302HCID 19931302, compoundHCID 178418339Butyllithium

Product 1

HCID 57528149HCID 57528149, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

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.

Workup

  1. customTo a 500-mL 3-necked round bottom flask equipped with a 250-mL pressure
  2. additionaddition funnel, a nitrogen inlet with thermocouple and an overhead stirrer
  3. additionwas then added slowly
  4. temperaturewith cooling over 1.5 hours
  5. additionwas carefully added
  6. stirringThe mixture was stirred for 1 hour at which time it
  7. washthe organics washed with water, brine
  8. dry with materialdried for 1 hour over anhydrous magnesium sulfate
  9. filtrationFiltration and removal of the solvent at reduced pressure
  10. customresulted in a light-colored oil which
  11. distillationwas distilled twice from Na2CO3 and phenothiazine through a based-washed 15-cm Vigreux

Sources & evidence

ORD record
ord-4d30c12d214441c4ad407dac1dee2e28
Source dataset
uspto-grants-2009_01
Patent number
US07476492B2

Reaction notes

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