Triethylamine → 1,1-Bis(trifluoromethyl)ethyl methacrylate

HRID 424320Notes

Reaction equation

HRID 424320 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]([CH3:9])([OH:8])[C:4]([F:7])([F:6])[F:5].C(N(CC)CC)C.[C:19](Cl)(=[O:23])[C:20]([CH3:22])=[CH2:21]>CN(C)C1C=CN=CC=1.CC(C)=O>[C:19]([O:8][C:3]([CH3:9])([C:4]([F:6])([F:5])[F:7])[C:2]([F:10])([F:11])[F:1])(=[O:23])[C:20]([CH3:22])=[CH2:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 739361,1,1,3,3,3-Hexafluoro-2-methylpropan-2-ol

Product 1

HCID 178164411,1-Bis(trifluoromethyl)ethyl methacrylateYield 74.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 180AcetoneSolvent

Procedure

7.3 g of 1,1,1,3,3,3-hexafluoro-2-methyl-2-propanol, 0.2 g of 4-dimethylaminopyridine, 4.9 g of triethylamine and 20 g of acetone were charged into a four-necked flask equipped with a stirrer, a thermometer and a dropping funnel, and were dissolved by stirring. Then, 4.6 g of methacrylic acid chloride was dropwise added to the resulting solution at about 5° C. over 30 minutes, followed by stirring at the same temperature for 3 hours. Thereafter, the reaction solution was washed with water, thereby obtaining 7.5 g of 1,1,1,3,3,3-hexafluoro-2-methyl-2-propyl methacrylate. The 1H-NMR data of the obtained 1,1,1,3,3,3-hexafluoro-2-methyl-2-propyl methacrylate were as follows.

Workup

  1. customequipped with a stirrer
  2. dissolutiona thermometer and a dropping funnel, and were dissolved
  3. stirringby stirring at the same temperature for 3 hours
  4. washThereafter, the reaction solution was washed with water

Sources & evidence

ORD record
ord-733f9dac74ec432387137e111617b79d
Source dataset
uspto-grants-2012_01
Patent number
US08105747B2

Reaction notes

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