Triethylamine → 2-Ethyl-2-methacryloyloxyadamantane

HRID 1369358

Reaction equation

HRID 1369358 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-9a8617f7ceab4cba9d7d1e46a274944a
Source dataset
uspto-grants-2003_06
Patent number
US06579659B2

Linked notes

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