Triethylamine → 2-Ethyl-2-methacryloyloxyadamantane

HRID 2298737Notes

Reaction equation

HRID 2298737 reaction equation
[CH2:1]([C:3]1([OH:13])[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2)[CH3:2].C(N(CC)CC)C.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23]>CC(CC(C)C)=O>[C:21]([O:13][C:3]1([CH2:1][CH3:2])[CH:4]2[CH2:12][CH:8]3[CH2:7][CH:6]([CH2:11][CH:10]1[CH2:9]3)[CH2:5]2)(=[O:25])[C:22]([CH3:24])=[CH2:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 44019512-Ethyl-2-adamantanol

Product 1

HCID 98136452-Ethyl-2-methacryloyloxyadamantaneYield 60%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

180 g of 2-Ethyl-2-adamantanol, 303 g of triethylamine and 500 g of methylisobutyl ketone were mixed by stirring at 90° C. While stirring, 157 g of methacrylic acid chloride was added dropwise to the mixture. After completion of the dropwise addition, the mixture was further stirred for 72 hours. Then, extraction and distillation were conducted to obtain 2-ethyl-2-adamantyl methacrylate at the yield of 60%.

Workup

  1. stirringWhile stirring
  2. additionAfter completion of the dropwise addition
  3. stirringthe mixture was further stirred for 72 hours
  4. extractionThen, extraction and distillation

Sources & evidence

ORD record
ord-124bd73fd62845988cea0e120ad74de7
Source dataset
uspto-grants-2002_12
Patent number
US06495307B2

Reaction notes

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