Methanol → HCID 13627533, compound

HRID 1589616Notes

Reaction equation

HRID 1589616 reaction equation
CO.[C:3]([C:5]1[C:10]([F:11])=[C:9]([F:12])[C:8]([OH:13])=[C:7]([F:14])[C:6]=1[F:15])#[N:4].[C:16](Cl)(=[O:20])[C:17]([CH3:19])=[CH2:18].O>[Na]>[C:16]([O:13][C:8]1[C:7]([F:14])=[C:6]([F:15])[C:5]([C:3]#[N:4])=[C:10]([F:11])[C:9]=1[F:12])(=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 13528Methacryloyl chlorideHCID 36133332,3,5,6-Tetrafluoro-4-hydroxybenzonitrile

Product 1

HCID 13627533HCID 13627533, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent2×

Procedure

In 50 ml of methanol having 0.94 g (0.0236 mol) of sodium hydroide dissolved therein, 3.0 g (0.0157 mol) of 4-cyano-2,3,5,6-tetrafluorophenol was dissolved. The resultant solution was kept with ice at 0° C. To the cooled solution, 1.80 g (0.0173 mol) of methacrylic acid chloride as slowly added dropwise. After completion of this dropwise addition, the resultant mixture was stirred at the same temperature for two hours. It was then mixed with 50 ml of pure water and adjusted to pH 10 by addition of an aqueous 20% sodium hydroide solution. As the result, white crystals occurred. The white crystals were filtered, washed with cold water, and then dried to obtain 1.35 g of 4-cyano-2,3,5,6-tetrafluorophenyl methacrylate (purity 98% and yield 32 mol % based on 4-cyano-2,3,5,6-tetrafluorophenol). The analyses obtained of this novel substance for the determination of its chemical structure were the same as those of Example 2.

Workup

  1. customwas kept with ice at 0° C
  2. additionAfter completion of this dropwise addition
  3. filtrationThe white crystals were filtered
  4. washwashed with cold water
  5. customdried

Sources & evidence

ORD record
ord-6a500dd9a41445308eaaf64a0b10a8aa
Source dataset
uspto-grants-1986_02
Patent number
US04572805

Reaction notes

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