Hydrochloric Acid → 2-Ethyl-3-(o-anisoyl)benzofuran

HRID 1681946Notes

Reaction equation

HRID 1681946 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1)[CH3:2].[C:12](Cl)(=[O:21])[C:13]1[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[CH:17][CH:18]=1.Cl[Sn]Cl.Cl>C1C=CC=CC=1.O>[CH2:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[C:7]=1[C:12](=[O:21])[C:13]1[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 765822-EthylbenzofuranHCID 889692-Methoxybenzoyl chloride

Product 1

HCID 123912692-Ethyl-3-(o-anisoyl)benzofuran

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

--To an ice cooled solution of 2-ethyl benzofuran 5.0 g and 5.9 g of o-anisoyl chloride dissolved in 20 ml benzene were added 4.1 ml of SnCl2 dropwise; the reaction mixture was stirred for 3 hours at room temperature. Then it was poured into water, 30 g, containing 5 ml of conc. HCl. The benzene layer was separated and the solution was extracted with benzene again. The combined benzene layer was washed with a 5% NaHCO3 solution and then with water. After drying and removal of benzene under reduced pressure, the yellowish oil, 2-ethyl-3-(o-anisoyl) benzofuran was obtained. Pyridine-HCl was prepared by the introduction of dried HCl gas to 4.75 g of pyridine and a 50 ml of benzene solution, and then by removing benzene twice.

Workup

  1. customThe benzene layer was separated
  2. extractionthe solution was extracted with benzene again
  3. washThe combined benzene layer was washed with a 5% NaHCO3 solution
  4. customAfter drying
  5. customremoval of benzene under reduced pressure

Sources & evidence

ORD record
ord-e45f714e5c7545f99cb7d313bf71381e
Source dataset
uspto-grants-1992_12
Patent number
US05175184

Reaction notes

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