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

HRID 1157147Notes

Reaction equation

HRID 1157147 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 (1b) (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
  4. filtrationthe precipitate was filtered
  5. customThe resulting solid was triturated twice with EtOH
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-f5c44d939a1744719716c455bb899d0f
Source dataset
uspto-grants-2010_10
Patent number
US07807670B2

Reaction notes

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