4-hydroxy-5-methyl-5-phenyl-3-phenylmethoxy-2-(5H)-furanone → 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

HRID 369137Notes

Reaction equation

HRID 369137 reaction equation
[OH:1][C:2]1[C:6]([CH3:13])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:14])[C:3]=1[O:15]CC1C=CC=CC=1>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[OH:15][C:3]1[C:4](=[O:14])[O:5][C:6]([CH3:13])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2]=1[OH:1]

Participants

4

Reactant 1

HCID 702488804-hydroxy-5-methyl-5-phenyl-3-phenylmethoxy-2-(5H)-furanone

Product 1

HCID 547254993,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

The 4-hydroxy-5-methyl-5-phenyl-3-phenylmethoxy-2-(5H)-furanone (1.2 g) was subjected to hydrogenation over 100 mg of 5% Pd/BaSO4 in 100 mL of MeOH at room temperature and under 30 psi H2. The reaction was monitored periodically by TLC analysis. The suspension was filtered through two #1 filter papers, concentrated to a white solid and recrystallized from MeOH/H2O to give 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone as a white crystalline material: mp 173-175° C. dec. 1H NMR (acetone-d6) δ 7.53-7.36 (m, 5H), 1.84 (s, 3H). Anal Calcd for C11H10O4 +0.125H2O): C, 63.38; H, 4.96. Found: C, 63.30; H, 4.96.

Workup

  1. filtrationThe suspension was filtered through two #1
  2. filtrationfilter papers
  3. concentrationconcentrated to a white solid
  4. customrecrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-e158ef800a1c460c91c0c7eca830759b
Source dataset
uspto-grants-2000_10
Patent number
US06136832

Reaction notes

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