Boric Acid → 3-(4-Methoxyphenylsulfonyl)acrylonitrile

HRID 2166671Notes

Reaction equation

HRID 2166671 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[Na+].C([O-])(=O)C.[Na+].B(O)(O)O.Cl[C:23](=[CH2:26])[C:24]#[N:25]>O.C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([CH:26]=[CH:23][C:24]#[N:25])(=[O:11])=[O:10])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 7628Boric AcidHCID 701982-ChloroacrylonitrileHCID 517045Sodium AcetateHCID 23680956Sodium 4-methoxybenzene-1-sulfinate

Product 1

HCID 536592353-(4-Methoxyphenylsulfonyl)acrylonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

In a flask, 59.5 g. (0.31 mole) sodium 4-methoxybenzenesulfinate, 25.4 g. (0.31 mole) sodium acetate and 19.2 g. (0.31 mole) boric acid were dissolved in a mixture of 150 ml. water and 275 ml. isopropyl alcohol. There was then added, with stirring, dropwise, 33.9 g. (31 ml., 0.39 mole) 2-chloroacrylonitrile. The mixture was stirred for some time at room temperature. Water was then added and the mixture stirred for one hour. A precipitate formed, which was filtered, washed with water and ethanol, and dried.

Workup

  1. additionThere was then added
  2. stirringThe mixture was stirred for some time at room temperature
  3. stirringthe mixture stirred for one hour
  4. customA precipitate formed
  5. filtrationwhich was filtered
  6. washwashed with water and ethanol
  7. customdried

Sources & evidence

ORD record
ord-681a74549a13414f9452a237da7e6ea3
Source dataset
uspto-grants-1983_06
Patent number
US04388249

Reaction notes

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