Acryloyl chloride → HCID 13627534, compound

HRID 1589618Notes

Reaction equation

HRID 1589618 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:17])[CH:15]=[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:17])[CH:15]=[CH2:16]

Participants

4

Reactant 2

HCID 13140Acryloyl chlorideHCID 36133332,3,5,6-Tetrafluoro-4-hydroxybenzonitrile

Product 1

HCID 13627534HCID 13627534, compoundYield 62%

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 11.3 g (0.125 mol) of acrylic acid chloride were dissolved. To the resultant solution, 20 g of molecular sieve 3 Å in diameter was added. The mixture was stirred under reflux for 38 hours. The resultant reaction mixture was cooled off and filtered to separate the molecular sieve. The filtrate was dried with magnesium sulfate and evaporated to dryness with a rotary evaporator. Consequently, there was obtained 15.2 g of 4-cyano-2,3,5,6-tetrafluorophenyl acrylate (yield 62.0% based on 4-cyano-2,3,5,6-tetrafluorophenol, purity 96.4%) having a melting point below determined.

Workup

  1. temperatureunder reflux for 38 hours
  2. customThe resultant reaction mixture
  3. temperaturewas cooled off
  4. filtrationfiltered
  5. customto separate the molecular sieve
  6. dry with materialThe filtrate was dried with magnesium sulfate
  7. customevaporated to dryness with a rotary evaporator

Sources & evidence

ORD record
ord-30b0eae3a0dd4aa8a2648f9d5e342602
Source dataset
uspto-grants-1986_02
Patent number
US04572805

Reaction notes

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