1,3-Indandione → 2-(3,4-dichlorobenzylidene)-1H-indene-1,3(2H)-dione

HRID 490786Notes

Reaction equation

HRID 490786 reaction equation
[C:1]1(=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:10])[CH2:2]1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:16]=O>CCO.N1CCCCC1>[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:16]=[C:2]1[C:1](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:10]

Participants

5

Reactant 2

HCID 118151,3-IndandioneHCID 227103,4-Dichlorobenzaldehyde

Product 1

HCID 75149132-(3,4-dichlorobenzylidene)-1H-indene-1,3(2H)-dioneYield 85%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of indan-1,3-dione (1a) (960 mg, 6.6 mmol) in EtOH (8.2 mL) was added 3,4-dichlorobenzaldehyde (b) (1.3 g 7.2 mmol) followed by piperidine (3 drops). The reaction mixture was heated to reflux for 30 min. After cooling the reaction was diluted with EtOH (8 mL) and the precipitate was filtered. The resulting solid was triturated twice with EtOH and dried under high vacuum to give 2-(3,4-dichloro-benzylidene)-indane-1,3-dione (1c) (1.7 g, 82% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 min
  3. temperatureAfter cooling the reaction
  4. filtrationthe precipitate was filtered
  5. customThe resulting solid was triturated twice with EtOH
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-3fe82cce85a548b6a1decef4096f02d3
Source dataset
uspto-grants-2009_05
Patent number
US07528167B2

Reaction notes

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