Methacryloyl chloride → 2-Ethyl-2-methacryloyloxyadamantane

HRID 2298730Notes

Reaction equation

HRID 2298730 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 64151Adamantanone2×HCID 178506846HCID 178506846, compound

Product 1

HCID 98136452-Ethyl-2-methacryloyloxyadamantane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To 31.1 g of 2-adamantanone was added 50 g of diethyl ether to form a solution. To the solution was added dropwise 200 ml of a solution of ethyllithium (at a concentration of 1.14 mol/L) in diethyl ether while keeping the solution at a temperature not higher than 10° C. After stirring for two hours at 0° C., methacrylic acid chloride in an amount of 26.2 g (1.2 times the molar amount of 2-adamantanone) was added dropwise to the solution while keeping the solution at a temperature not higher than 10° C. After the dropwise addition was completed, the resulting mixture was stirred for about 12 hours at room temperature. Thereafter, the precipitated organic salt was filtered off. The resulting organic layer was washed with anqueous solution of 5 wt % sodium bicarbonate and then washed with water twice. The organic layer was concentrated and then distilled under reduced pressure to obtain 2-ethyl-2-adamantyl methacrylate represented by the following formula.

Workup

  1. customto form a solution
  2. customhigher than 10° C
  3. customhigher than 10° C
  4. additionAfter the dropwise addition
  5. stirringthe resulting mixture was stirred for about 12 hours at room temperature
  6. filtrationThereafter, the precipitated organic salt was filtered off
  7. washThe resulting organic layer was washed with anqueous solution of 5 wt % sodium bicarbonate
  8. washwashed with water twice
  9. concentrationThe organic layer was concentrated
  10. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-dc1a763143a74722b04cd31f76a474c3
Source dataset
uspto-grants-2002_12
Patent number
US06495306B2

Reaction notes

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