Methacryloyl chloride → 2-Ethyl-2-methacryloyloxyadamantane

HRID 1979023Notes

Reaction equation

HRID 1979023 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.[CH2:12]([Li])[CH3:13].[C:15](Cl)(=[O:19])[C:16]([CH3:18])=[CH2:17]>C(OCC)C>[C:15]([O:11][C:2]1([CH2:12][CH3:13])[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)(=[O:19])[C:16]([CH3:18])=[CH2:17]

Participants

5

Reactant 3

HCID 13528Methacryloyl chlorideHCID 64151AdamantanoneHCID 178506846HCID 178506846, compound

Product 1

HCID 98136452-Ethyl-2-methacryloyloxyadamantaneYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

50 g of diethyl ether was added to 31.1 g of 2-adamantanone to prepare a solution. Then, 200 ml of a diethyl ether solution containing ethyl lithium in a concentration of 1.14 mole/L was added dropwise thereto at such a rate as to keep the temperature of the solution not exceeding 10° C. After stirring the solution thus obtained at 0° C. for 2 hours, 26.2 g of methacrylic acid chloride (1.2 mole times with respect to 2-adamantanone) was added dropwise thereto at such a rate as to keep the temperature not exceeding 10° C. After the completion of dropwise addition, the resulting solution was stirred at room temperature for 12 hours. Thereafter, the deposited inorganic salts were separated by filtration, and the organic layer was washed with a 5% by weight aqueous solution of sodium bicarbonate, followed by washing with water for 2 times. The organic layer was concentrated, and then subjected to distillation under reduced pressure to obtain 2-ethyl-2-adamantyl methacrylate represented by the following formula in a 60% yield.

Workup

  1. customto prepare a solution
  2. additionwas added dropwise
  3. customexceeding 10° C
  4. customthus obtained at 0° C. for 2 hours
  5. customexceeding 10° C
  6. additionAfter the completion of dropwise addition
  7. stirringthe resulting solution was stirred at room temperature for 12 hours
  8. customThereafter, the deposited inorganic salts were separated by filtration
  9. washthe organic layer was washed with a 5% by weight aqueous solution of sodium bicarbonate
  10. washby washing with water for 2 times
  11. concentrationThe organic layer was concentrated
  12. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-2405849fde5942eea7948ed401bf534e
Source dataset
uspto-grants-2001_05
Patent number
US06239231B1

Reaction notes

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