Benzaldehyde → 5-Methoxy-2-(1-phenylmethylidene)-2,3-dihydro-3-benzo[b]furanone

HRID 1857558Notes

Reaction equation

HRID 1857558 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:20]=[CH:19][C:14]2[O:15][CH2:16][C:17](=[O:18])[C:13]=2[CH:12]=1>ClCCl>[CH3:9][O:10][C:11]1[CH:20]=[CH:19][C:14]2[O:15][C:16](=[CH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:17](=[O:18])[C:13]=2[CH:12]=1

Participants

4

Reactant 2

HCID 240BenzaldehydeHCID 3466085-Methoxybenzofuran-3(2H)-one

Product 1

HCID 453564975-Methoxy-2-(1-phenylmethylidene)-2,3-dihydro-3-benzo[b]furanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

36.5 mmol (3.9 g) of benzaldehyde are added to a solution of 30.5 mmol (5 g) of 5-methoxy-3-benzo[b]furanone in 150 ml of dichloromethane. With vigorous stirring and at ambient temperature, 25 g of basic alumina are then added. Stirring is maintained at ambient temperature for 30 minutes. The mixture is then filtered, the filtrate is concentrated and the residue obtained is washed with a minimum amount of ethanol to yield the expected compound. Melting point: 134° C.

Workup

  1. addition25 g of basic alumina are then added
  2. stirringStirring
  3. temperatureis maintained at ambient temperature for 30 minutes
  4. filtrationThe mixture is then filtered
  5. concentrationthe filtrate is concentrated
  6. customthe residue obtained
  7. washis washed with a minimum amount of ethanol

Sources & evidence

ORD record
ord-470c924af9f3481497758ed57460230e
Source dataset
uspto-grants-2000_11
Patent number
US06147110

Reaction notes

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