Thionyl Chloride → 4,5-DICHLORO-2,3-DIHYDRO-1H-INDEN-1-ONE

HRID 1489026Notes

Reaction equation

HRID 1489026 reaction equation
ClC1C(Cl)=C2C(CCC2=O)=CC=1.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:21][CH2:22][C:23]([OH:25])=O.S(Cl)(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]2[C:15]=1[CH2:21][CH2:22][C:23]2=[O:25]

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 6451240Aluminum(III) ChlorideHCID 125951013-(2,3-Dichlorophenyl)propanoic acidHCID 219860816,7-Dichloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 229036224,5-DICHLORO-2,3-DIHYDRO-1H-INDEN-1-ONE

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 4,5-dichloro-1-indanone is prepared as in Example 15 for the preparation of 6,7-dichloro-1-indanone but star6ing with 26 g of 3-(2,3-dichlorophenyl)propionic acid, 138 ml of thionyl chloride, 550 ml of anhydrous dichloromethane and 20.5 g of aluminium chloride. After recrystallization from 100 ml of boiling ethanol, 12.67 g of 4,5-dichloro-1-indanone are thus obtained which melt at 78° C.

Workup

  1. customAfter recrystallization from 100 ml of boiling ethanol, 12.67 g of 4,5-dichloro-1-indanone
  2. customare thus obtained which melt at 78° C.

Sources & evidence

ORD record
ord-217cfdc3855e4f09968b1529914f0f7b
Source dataset
uspto-grants-1997_10
Patent number
US05677306

Reaction notes

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