Ethanol → 2(3H)-Benzofuranone

HRID 389792Notes

Reaction equation

HRID 389792 reaction equation
O[C:2]1[CH:7]=[CH:6][O:5][C:4](=[O:8])[C:3]=1[CH3:9].[CH2:10](O)[CH3:11]>P([O-])([O-])([O-])=O>[O:5]1[C:6]2[CH:7]=[CH:2][CH:10]=[CH:11][C:9]=2[CH2:3][C:4]1=[O:8]

Participants

4

Reactant 2

HCID 702EthanolHCID 546816204-Hydroxy-3-methyl-2H-pyran-2-one

Product 1

HCID 683822(3H)-Benzofuranone

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

0.40 g of the compound (7.4) are dissolved together with 0.175 g of 4-hydroxy-methyl-pyranone (Fluka) in 40 mL of phosphate buffer (0.2M, pH=5) at room temperature, and 20.0 mg of laccase (Trametes versicolor (Fluka)) are added. For better solubility, 1 mL of ethanol is also added. The mixture is stirred in an open vessel until the starting materials can no longer be detected (about 2 days). The mixture is concentrated and the residue is taken up in methanol and centrifuged. The desired product (211 mg) is obtained in the form of a brownish-beige solid. The product can be purified further by reprecipitation from ether/methanol mixtures.

Workup

  1. addition20.0 mg of laccase (Trametes versicolor (Fluka)) are added
  2. custom(about 2 days)
  3. concentrationThe mixture is concentrated

Sources & evidence

ORD record
ord-852ce7b7c7f846cd819e68fcb6168964
Source dataset
uspto-grants-2013_02
Patent number
US08383088B2

Reaction notes

Loading…