Acetone → HCID 53905017, compound

HRID 1904881Notes

Reaction equation

HRID 1904881 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=[CH:11][C:12]([OH:14])=[O:13].[CH2:15]([N:17](CC)CC)[CH3:16].CC(C)=O.ClCC#N>O>[C:15]([CH2:16][O:13][C:12](=[O:14])[CH:11]=[CH:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1)#[N:17]

Participants

6

Reactant 4

HCID 180AcetoneHCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 53405764HCID 53405764, compound

Product 1

HCID 53905017HCID 53905017, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

171.8 g of β-(2-benzofuryl)acrylic acid, synthesized in the manner as described in J. Chinese Chem. Soc. sev. II 8, pp. 374-379, and 101.5 g of triethylamine were added to 550 ml of acetone, to the mixture were added dropwise 75.9 g of chloroacetonitrile, and the mixture was refluxed by heating over a period of five hours. After the reaction, 400 ml of water were added to cool the reaction system, and the deposited crystals were filtered by a suction filter and then washed. The obtained crystals were recrystallized from acetone to thereby obtain 187 g of β-(2-benzofuryl)acrylic acid cyanomethyl ester having a melting point between 119° C. and 121° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating over a period of five hours
  3. additionwere added
  4. temperatureto cool the reaction system
  5. filtrationthe deposited crystals were filtered by a suction
  6. filtrationfilter
  7. washwashed
  8. customThe obtained crystals were recrystallized from acetone

Sources & evidence

ORD record
ord-100cf45612b14b29849ff1a2b7d4d189
Source dataset
uspto-grants-1989_06
Patent number
US04840869

Reaction notes

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