1,3-Dichlorobenzene → HCID 23369785, compound

Reaction equation

C([O:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:18])=[C:8]([NH:10][C:11](=[O:17])[C:12](=O)[CH:13]([CH3:15])C)[CH:9]=1)C.[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:24]1C=CC=C(Cl)C=1>>[OH:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:18])=[C:8]2[C:9]=1[C:13]([CH3:15])=[C:12]([CH3:24])[C:11](=[O:17])[NH:10]2

Participants

Reactant 3

HCID 109431,3-Dichlorobenzene

HCID 6451240Aluminum(III) Chloride

HCID 23369854HCID 23369854, compound

Product 1

HCID 23369785HCID 23369785, compoundYield 46.2%

Procedure

N-(5-ethoxy-2-methylphenyl)-2-oxo-3-methylbutanamide (8.8 g, 35.3 mmol) was dissolved in m-dichlorobenzene (100 ml). Aluminum chloride (20.6 g, 155 mmol) was added to the solution, and the mixture was placed in a bath of 100° C. and stirred for 1.5 hours. The reaction mixture was poured in ice--water, and the precipitate was collected by filtration. To the filtrate, a mixture of chloroform--methanol (5:1) was added. The organic phase was extracted, and dried. The solvent was distilled off under reduced pressure. The resultant residue was recrystallized from methanol--ether to obtain 3.3 g in total of the title compound as yellow powder (46.2%).