Triethylamine → 2-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)

HRID 2298736Notes

Reaction equation

HRID 2298736 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:23])[CH:21]=[CH2:22]>CC(CC(C)C)=O>[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:23])[CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 1365452-Methyl-2-adamantanol

Product 1

HCID 112182922-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)Yield 92%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

166 g of 2-Methyl-2-adamantanol, 303 g of triethylamine and 500 g of methylisobutyl ketone were mixed by stirring at 60° C. While stirring, 136 g of acrylic acid chloride was added dropwise to the mixture. After completion of the dropwise addition, the mixture was stirred for six more hours. Then, extraction and distillation were conducted to obtain 2-methyl-2-adamantyl acrylate at the yield of 92%.

Workup

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

Sources & evidence

ORD record
ord-164987de420a41ae9d49585da5afbb73
Source dataset
uspto-grants-2002_12
Patent number
US06495307B2

Reaction notes

Loading…