4-Hydroxy-3-(3-oxo-1,3-dihydro-isobenzofuran-1-yl)-chromen-2-one → 2-(4-Hydroxy-2-oxo-2H-chromen-3-ylmethyl)-benzoic acid

HRID 857528Notes

Reaction equation

HRID 857528 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[C:3]=1[CH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[O:14]1>C(O)C.[Pd]>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[C:3]=1[CH2:13][C:21]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[C:15]([OH:22])=[O:14]

Participants

4

Reactant 1

HCID 547064474-Hydroxy-3-(3-oxo-1,3-dihydro-isobenzofuran-1-yl)-chromen-2-one

Product 1

HCID 547064482-(4-Hydroxy-2-oxo-2H-chromen-3-ylmethyl)-benzoic acidYield 82.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution 4-Hydroxy-3-(3-oxo-1,3-dihydro-isobenzofuran-1-yl)-chromen-2-one (60 mg) in ethanol was added 10% Pd/C (10 mg) then stirred under a hydrogen balloon for 12 hours. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to give 2-(4-Hydroxy-2-oxo-2H-chromen-3-ylmethyl)-benzoic acid as white solid (50 mg). MS: 295[M−H].

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-74f71e1e158a4484a882f49dbd4d9bae
Source dataset
uspto-grants-2006_12
Patent number
US07145020B2

Reaction notes

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