Chloroacetone → 1-(3-Ethyl-1-benzofuran-2-yl)ethanone

HRID 1740721Notes

Reaction equation

HRID 1740721 reaction equation
O[CH:2]([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.Cl[CH2:13][C:14](=[O:16])[CH3:15].[OH-:17].[K+]>C(O)C>[C:14]([C:13]1[O:17][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:3]=1[CH2:2][CH3:11])(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 14797Potassium HydroxideHCID 1011212-Hydroxy-1-phenyl-1-propanone

Product 1

HCID 38603281-(3-Ethyl-1-benzofuran-2-yl)ethanoneYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reaction of hydroxypropiophenone (II) with chloroacetone (III) using potassium hydroxide in ethanol gives, by Stroemer-Schaefer condensation, 2-acetyl-3-ethylbenzofuran (IVj, R1 -R4 =H, R5 =C2H5, R6 =CH3) in a yield of about 80% (Belgian Patent Specification 553 621; (Chem. Abs. 5, 22016)).

Sources & evidence

ORD record
ord-bc65c71016fb46ccafd861828f1cb05a
Source dataset
uspto-grants-1999_10
Patent number
US05972878

Reaction notes

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