Triethylamine → 2-Methyl-2-adamantyl methacrylate

HRID 1979022Notes

Reaction equation

HRID 1979022 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-adamantanol

Product 1

HCID 98375662-Methyl-2-adamantyl methacrylateYield 75%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

83.1 g of 2-methyl-2-adamantanol and 101 g of triethylamine were charged, and 200 g of methyl isobutyl ketone was added thereto to prepare a solution. Then, 78.4 g of methacrylic acid chloride (1.5 mole times with respect to 2-methyl-2-adamantanol) was added dropwise thereto, followed by stirring at room temperature for 10 hours. After filtration, 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-methyl-2-adamantyl methacrylate represented by the following formula in a 75% yield.

Workup

  1. customto prepare a solution
  2. filtrationAfter filtration
  3. washthe organic layer was washed with a 5% by weight aqueous solution of sodium bicarbonate
  4. washby washing with water for 2 times
  5. concentrationThe organic layer was concentrated
  6. distillationsubjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-de9b439bf69b4cd88aaadd1fc075b1f1
Source dataset
uspto-grants-2001_05
Patent number
US06239231B1

Reaction notes

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