Ethanol → 4-Hydroxy-3-(3-oxo-1,3-dihydro-isobenzofuran-1-yl)-chromen-2-one

HRID 857527Notes

Reaction equation

HRID 857527 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])[CH:3]=1.[CH3:13][CH2:14][OH:15]>O>[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:14]1[C:13]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2](=[O:1])[O:15]1

Participants

4

Reactant 2

HCID 702EthanolHCID 546829304-Hydroxycoumarin

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 4-hydroxy-chromen-2-one (650 mg) and 2-carboxybenzyladehyde (300 mg) in EtOH was heated to reflux for 4 hours, cooled to room temperature then concentrated in vacuo to give a crude oil, which was diluted with water. The precipitated 4-hydroxy-chromen-2-one was collected by filtration (490 mg). A second crop of solid was collected from the mother liquor and triturated with hot EtOAc and filtered to provide 4-Hydroxy-3-(3-oxo-1,3-dihydro-isobenzofuran-1-yl)-chromen-2-one as white solid. MS: 293 [M−H].

Workup

  1. temperatureto reflux for 4 hours
  2. concentrationthen concentrated in vacuo
  3. customto give a crude oil, which
  4. filtrationThe precipitated 4-hydroxy-chromen-2-one was collected by filtration (490 mg)
  5. customA second crop of solid was collected from the mother liquor
  6. customtriturated with hot EtOAc
  7. filtrationfiltered

Sources & evidence

ORD record
ord-2bef73997a2c448daafed1a7636d10c1
Source dataset
uspto-grants-2006_12
Patent number
US07145020B2

Reaction notes

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