Hydrochloric Acid → HCID 11687622, compound

HRID 418824Notes

Reaction equation

HRID 418824 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[CH:7][C:6]2=[O:20].C([O-])(=[O:23])C.[K+].C([O-])([O-])=O.[K+].[K+].Cl>O1CCOCC1.CN(C=O)C.O.CO.C1COCC1>[OH:23][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)=[CH:7][C:6]2=[O:20]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 66650401HCID 66650401, compound

Product 1

HCID 11687622HCID 11687622, compoundYield 42%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 217120691,4-dioxane N,N-dimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-bromomethyl-2-(4-hydroxyphenyl)chromen-4-one (250 mg, 0.754 mmol) in dioxane:DMF (10:2, 12 mL), was added potassium acetate (500 mg, 3.77 mmol). The mixture was heated at 100° C. for 3 h. The reaction mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated to give crude product (225 mg, 96%). To a solution of the crude product (220 mg, 0.711 mmol) in MeOH:THF (5 mL:5 mL) was added K2CO3 (216 mg, 1.56 mmol) and the mixture was stirred for 24 h at rt. Then the reaction mixture was neutralized by dilute HCl and extracted by EtOAc, the combined organic layers were washed with water, brine, dried and concentrated to give a crude product, which was purified by column chromatography using 5% MeOH in dichloromethane, to afford 6-hydroxymethyl-2-(4-hydroxyphenyl)chromen-4-one (80 mg, 42%). MS (ES) m/z: 269.88 (M+1), 268.85 (M); Mp. 246-247° C.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give crude product (225 mg, 96%)
  6. extractionextracted by EtOAc
  7. washthe combined organic layers were washed with water, brine
  8. customdried
  9. concentrationconcentrated
  10. customto give a crude product, which
  11. customwas purified by column chromatography

Sources & evidence

ORD record
ord-fbaac03cf5314379b5caf8c25723d61a
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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