Methacryloyl chloride → 2-Ethyl-2-methacryloyloxyadamantane

HRID 2186645Notes

Reaction equation

HRID 2186645 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-methacryloyloxyadamantane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

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

Workup

  1. customto form a solution
  2. additionwas added dropwise
  3. customexceeding 10° C
  4. customexceeding 10° C
  5. additionAfter the completion of addition
  6. stirringthe solution was stirred at room temperature for 12 hours
  7. customwere removed by filtration
  8. washThe organic layer was washed with a 5% by weight aqueous solution of sodium bicarbonate
  9. washwashed twice with water
  10. concentrationThe organic layer was concentrated
  11. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-a0e2b1f5d480469ca035fda5c63ae0e8
Source dataset
uspto-grants-2002_06
Patent number
US06406830B2

Reaction notes

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