Triethylamine → 2-Methyl-2-adamantyl methacrylate

HRID 2298729Notes

Reaction equation

HRID 2298729 reaction equation
[CH3:1][C:2]1([OH:12])[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.C(N(CC)CC)C.[C:20](Cl)(=[O:24])[C:21]([CH3:23])=[CH2:22]>C(C(C)=O)C(C)C>[C:20]([O:12][C:2]1([CH3:1])[CH:3]2[CH2:11][CH:7]3[CH2:6][CH:5]([CH2:10][CH:9]1[CH2:8]3)[CH2:4]2)(=[O:24])[C:21]([CH3:23])=[CH2:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 1365452-Methyl-2-adamantanol2×

Product 1

HCID 98375662-Methyl-2-adamantyl methacrylate

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A vessel was charged with 83.1 g of 2-methyl-2-adamantanol and 101 g of triethylamine, and 200 g of methyl isobutyl ketone was added thereto to form a solution. To the solution was added dropwise 78.4 g of methacrylic acid chloride(1.5 times the molar amount of 2-methyl-2-adamantanol), followed by stirring for about 10 hours at room temperature. After filtration, the resulting organic layer was washed with an aqueous 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-methyl-2-adamantyl methacrylate represented by the following formula.

Workup

  1. additionwas added
  2. customto form a solution
  3. filtrationAfter filtration
  4. washthe resulting organic layer was washed with an aqueous solution of 5 wt % sodium bicarbonate
  5. washwashed with water twice
  6. concentrationThe organic layer was concentrated
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-f737964e07bd43e394ec85f382a03d4f
Source dataset
uspto-grants-2002_12
Patent number
US06495306B2

Reaction notes

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