Aluminum(III) Chloride → 8-chloro-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-5-one

HRID 544675Notes

Reaction equation

HRID 544675 reaction equation
[Cl:1][C:2]1[C:3]([CH2:14][CH2:15][C:16](Cl)=[O:17])=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[Cl:1][C:2]1[C:3]2[CH2:14][CH2:15][C:16](=[O:17])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 133207033-(3-Chloro[1,1'-biphenyl]-2-yl)propanoyl chloride

Product 1

HCID 204033458-chloro-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-5-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a manner similar to that of W. S. Johnson and H. J. Glenn, J. Am. Chem. Soc., 71, 1092 (1949), the reaction of 3-(3-chloro[1,1'-biphenyl]-2-yl)propanoyl chloride (5.3 grams, 0.019 mole), aluminum chloride (3.33 grams, 0.025 mole) and benzene (125 ml) gave a brown oil. The oil was subjected to column chromatography on silica gel and eluted with 9:1 chloroform:petroleum ether to give 8-chloro-6,7-dihydro-5H-dibenzo[a,c]cycloheptene-5-one as a solid.

Workup

  1. customgave a brown oil
  2. washeluted with 9:1 chloroform

Sources & evidence

ORD record
ord-8c445373857a46e6aed9bde94cc1fe45
Source dataset
uspto-grants-1984_05
Patent number
US04451484

Reaction notes

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