Methacryloyl chloride → HCID 13627533, compound

HRID 1589615Notes

Reaction equation

HRID 1589615 reaction equation
[C:1]([C:3]1[C:8]([F:9])=[C:7]([F:10])[C:6]([OH:11])=[C:5]([F:12])[C:4]=1[F:13])#[N:2].[C:14](Cl)(=[O:18])[C:15]([CH3:17])=[CH2:16]>C(Cl)(Cl)(Cl)Cl>[C:14]([O:11][C:6]1[C:5]([F:12])=[C:4]([F:13])[C:3]([C:1]#[N:2])=[C:8]([F:9])[C:7]=1[F:10])(=[O:18])[C:15]([CH3:17])=[CH2:16]

Participants

4

Reactant 2

HCID 13528Methacryloyl chlorideHCID 36133332,3,5,6-Tetrafluoro-4-hydroxybenzonitrile

Product 1

HCID 13627533HCID 13627533, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

In 200 ml of carbon tetrachloride, 19.1 g (0.100 mol) of 4-cyano-2,3,5,6-tetrafluorophenol and 13.0 g (0.125 mol) of methacrylic acid chloride were dissolved. To the resultant solution was added 20 g of molecular sieve 3 Å in diameter. The resultant mixture was refluxed as agitated for 48 hours. The reaction mixture so produced was cooled and then filtered to separate the molecular sieve. The filtrate was dried with magnesium sulfate and then evaporated to dryness with a rotary evaporator. Consequently, there was obtained 21.7 g of 4-cyano-2,3,5,6-tetrafluorophenyl methacrylate (yield 83.8% based on 4-cyano-2,3,5,6-tetrafluorophenol, purity 96.5%).

Workup

  1. customThe reaction mixture so produced
  2. temperaturewas cooled
  3. filtrationfiltered
  4. customto separate the molecular sieve
  5. dry with materialThe filtrate was dried with magnesium sulfate
  6. customevaporated to dryness with a rotary evaporator

Sources & evidence

ORD record
ord-f5d1d169c0c448b887376a42aed92100
Source dataset
uspto-grants-1986_02
Patent number
US04572805

Reaction notes

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