Hydroquinone → 5-hydroxy-3-phenyl-3H-benzofuran-2-one

HRID 1109265Notes

Reaction equation

HRID 1109265 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[C:9](O)(=[O:18])[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)O.S(=O)(=O)(O)O>C(O)(=O)C>[OH:2][C:1]1[CH:8]=[CH:7][C:5]2[O:6][C:9](=[O:18])[CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 1118Sulfuric AcidHCID 1292Mandelic Acid

Product 1

HCID 106329835-hydroxy-3-phenyl-3H-benzofuran-2-oneYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of hydroquinone (15 g), mandelic acid (15 g), acetic acid (95 cm3) and sulphuric acid (5 cm3) was stirred at ambient temperature before filtering off solid material. The solid was washed with water and dried to give 5-hydroxy-2-oxo-3-phenyl-2,3-dihydrobenzofuran (14 g, 65%).

Workup

  1. filtrationbefore filtering off solid material
  2. washThe solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-33ad51b4a52043a58c000efc318eaf30
Source dataset
uspto-grants-1994_06
Patent number
US05319109

Reaction notes

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