6-hydroxy-7-methoxybenzofuran-3(2H)-one → 2,3-Dihydro-7-methoxy-6-benzofuranol

HRID 25899Notes

Reaction equation

HRID 25899 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=O)[CH2:7][O:8][C:4]=2[C:3]=1[O:12][CH3:13]>[Pd].C(O)(=O)C>[CH3:13][O:12][C:3]1[C:4]2[O:8][CH2:7][CH2:6][C:5]=2[CH:10]=[CH:11][C:2]=1[OH:1]

Participants

4

Reactant 1

HCID 218565766-hydroxy-7-methoxybenzofuran-3(2H)-one

Product 1

HCID 218565712,3-Dihydro-7-methoxy-6-benzofuranol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 6-hydroxy-7-methoxy-3(2H)-benzofuranone, 233 mg. (1.29 mmole) in 5 ml. of acetic acid was hydrogenated for 4 hours at room temperature under 53 psi of H2 using 50 mg. of 10% Pd/C as catalyst. The mixture was then filtered, concentrated in vacuo to a residue which was chromatographed over silica gel (E. Merck 60) eluting with CHCl3 to yield, after evaporation, a colorless oil.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated in vacuo to a residue which
  3. customwas chromatographed over silica gel (E. Merck 60)
  4. washeluting with CHCl3
  5. customto yield
  6. customafter evaporation

Sources & evidence

ORD record
ord-72ccb175be7d47e893f8af003ff03be5
Source dataset
uspto-grants-1979_04
Patent number
US04147703

Reaction notes

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