Benzaldehyde → 2-Benzylidene-1,3-indandione

HRID 1859077

Reaction equation

HRID 1859077 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.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1C=CC=CC=1.N1CCCCC1>[CH:12](=[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])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 240BenzaldehydeHCID 118151,3-Indandione

Product 1

HCID 2378222-Benzylidene-1,3-indandioneYield 72.1%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

To a solution of 1,3-indandione (43.8 g) and piperidine (44 mg) in dry benzene (500 ml) was added benzaldhyde (31.8 g). The mixture was heated to reflux and the water generated was removed by Dean-Stark trap. After 24 hours, the mixture was evaporated to dryness. The residue was recrystallized from ethanol (200 ml) to give 2-benzylidene-1,3-indandione as a yellow solid (50.6 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customthe water generated was removed by Dean-Stark trap
  4. customthe mixture was evaporated to dryness
  5. customThe residue was recrystallized from ethanol (200 ml)

Sources & evidence

ORD record
ord-4cdc2d56b9d643e9bb22b4106b8ec394
Source dataset
uspto-grants-2000_11
Patent number
US06153645

Linked notes

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