Hydrochloric Acid → 2-Butyl-1-benzofuran-3(2H)-one

HRID 1611056Notes

Reaction equation

HRID 1611056 reaction equation
C([O:4][C:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][C:6]=1[CH2:14][CH2:15][CH2:16][CH3:17])(=O)C.Cl.[OH-].[Na+]>C(O)C>[CH2:14]([CH:6]1[C:5](=[O:4])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7]1)[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10243019658053-37-3

Product 1

HCID 30208472-Butyl-1-benzofuran-3(2H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4.6 g of 3-acetoxy-2-(n-butyl)benzofuran were dissolved in 20 ml of ethanol in a 100 ml flask, and 20 ml 6N hydrochloric acid were added. The mixture was heated to reflux for 4 hours. After cooling to room temperature, the pH was adjusted to 4 to 6 with sodium hydroxide, and the ethanol was distilled off. This was followed by extraction with dichloromethane. Drying of the combined organic phases over sodium sulphate and removal of the solvent resulted in 2.8 g (76% of theory) of 2-(n-butyl)-3(2H)-benzofuranone as yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. distillationthe ethanol was distilled off
  4. extractionThis was followed by extraction with dichloromethane
  5. dry with materialDrying of the combined organic phases over sodium sulphate and removal of the solvent
  6. customresulted in 2.8 g (76% of theory) of 2-(n-butyl)-3(2H)-benzofuranone as yellow oil

Sources & evidence

ORD record
ord-7edd15ce172e4258a750c0a67865e993
Source dataset
uspto-grants-2006_01
Patent number
US06984741B2

Reaction notes

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