Triethylamine → 2-Methyladamantan-2-yl Acrylate (stabilized with MEHQ)
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
Product 1
Reagents, catalysts & solvents 1
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
- stirringWhile stirring
- additionAfter completion of the dropwise addition
- stirringthe mixture was stirred for six more hours
- extractionThen, extraction and distillation
Sources & evidence
- ORD record
- ord-f774d4603a0442d0bdca4e7132dd665b
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06579659B2
Reaction notes
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