Sodium Acetate → HCID 11651889, compound

HRID 418834Notes

Reaction equation

HRID 418834 reaction equation
Br[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C([O-])(=[O:23])C.[Na+]>CC(O)=O>[OH:23][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 66650305HCID 66650305, compound

Product 1

HCID 11651889HCID 11651889, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-bromomethyl-2-(4-hydroxyphenyl)-4H-chromen-4-one (0.50 g, 1.5 mmol) and sodium acetate (1.24 g, 15.0 mmol) in AcOH (20 mL) was heated to reflux for 15 h. AcOH was removed and the residue was poured into water and extracted with EtOAc (100 mL). The organic phase was further washed with brine and dried over sodium sulfate. The residue was mixed with potassium carbonate (0.52 g) and MeOH (10 mL) and stirred for 2 h. AcOH (1.0 mL) was added and MeOH was removed. The residue was poured into water and the solid was washed additionally with water and hexane to give 3-(hydroxymethyl)-2-(4-hydroxyphenyl)-4H-chromen-4-one (0.265 g, 62.6%). MS (ES) m/z: 269.94 (M+1), 268.94 (M); Mp. 234-235° C.

Workup

  1. temperatureto reflux for 15 h
  2. customAcOH was removed
  3. additionthe residue was poured into water
  4. extractionextracted with EtOAc (100 mL)
  5. washThe organic phase was further washed with brine
  6. dry with materialdried over sodium sulfate
  7. additionThe residue was mixed with potassium carbonate (0.52 g) and MeOH (10 mL)
  8. additionAcOH (1.0 mL) was added
  9. customMeOH was removed
  10. additionThe residue was poured into water
  11. washthe solid was washed additionally with water and hexane

Sources & evidence

ORD record
ord-cd362d1c669041ba8761d8afa3d01cfa
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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