Thionyl Chloride → 2-(5-Chloro-2,3-dihydro-2-oxo-3-phenyl-3-benzofuranyl)acetyl chloride

HRID 1723176Notes

Reaction equation

HRID 1723176 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12](=[O:14])[C:11]([CH2:21][C:22](O)=[O:23])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]=2[CH:25]=1>C1C=CC=CC=1>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12](=[O:14])[C:11]([CH2:21][C:22]([Cl:3])=[O:23])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]=2[CH:25]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 143034932-(5-Chloro-2,3-dihydro-2-oxo-3-phenyl-3-benzofuranyl)acetic acid

Product 1

HCID 143034982-(5-Chloro-2,3-dihydro-2-oxo-3-phenyl-3-benzofuranyl)acetyl chlorideYield 96.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

23.7 g of double-distilled thionyl chloride are added dropwise to a solution, stirred and heated to 70° C., of 30.2 g of 2-(5-chloro-2,3-dihydro-2-oxo-3-phenyl-3-benzofuranyl)acetic acid in 250 ml of anhydrous benzene. When the addition is complete, the mixture is heated to reflux until the evolution of gas has completely ceased. The medium is concentrated under vacuum, the residue washed with 200 ml of anhydrous benzene and the solvent evaporated off. This operation is repeated twice and the product is left to crystallize at room temperature. The crystals are washed with petroleum ether and filtered off, and 31 g of pure product are obtained.

Workup

  1. additionWhen the addition
  2. temperaturethe mixture is heated
  3. temperatureto reflux until the evolution of gas
  4. concentrationThe medium is concentrated under vacuum
  5. washthe residue washed with 200 ml of anhydrous benzene
  6. customthe solvent evaporated off
  7. waitthe product is left
  8. customto crystallize at room temperature
  9. washThe crystals are washed with petroleum ether
  10. filtrationfiltered off

Sources & evidence

ORD record
ord-19ec3772f90d471db809d3f5cfdc8773
Source dataset
uspto-grants-1989_08
Patent number
US04859700

Reaction notes

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