Water → HCID 23103555, compound

HRID 230895Notes

Reaction equation

HRID 230895 reaction equation
C([CH2:4][O:5][C:6]1[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[C:7]=1[C:8](=O)[CH:9]=[CH:10][CH:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:13][CH2:12]1)(O)=O.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.O>C(O)(=O)C>[OH:27][C:23]1[C:7]2[C:8]([CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH2:20][OH:21])=[CH:15][CH:16]=3)=[CH:4][O:5][C:6]=2[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 67135955HCID 67135955, compound

Product 1

HCID 23103555HCID 23103555, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

To a solution of 2′-carboxymethoxy-6′-hydroxy-4-(3-hydroxypropoxy)dihydrochalcone (2.8 g) in acetic acid (39.4 mL) were added sodium acetate (17.8 g) and acetic anhydride (17.9 mL), and the mixture was stirred at 115° C. overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethylether. The extract was washed with water twice, a saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in methanol (10 mL). To the solution was added 2 mol/L aqueous sodium hydroxide solution (26 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was acidified by addition of 2 mol/L hydrochloric acid, and the resulting mixture was extracted with diethyl ether. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-1/1) to give the title compound (0.45 g).

Workup

  1. extractionthe resulting mixture was extracted with diethylether
  2. washThe extract was washed with water twice
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution, water and brine successively, and dried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe residue was dissolved in methanol (10 mL)
  6. additionTo the solution was added 2 mol/L aqueous sodium hydroxide solution (26 mL)
  7. stirringthe mixture was stirred at room temperature for 3 hours
  8. additionThe reaction mixture was acidified by addition of 2 mol/L hydrochloric acid
  9. extractionthe resulting mixture was extracted with diethyl ether
  10. washThe extract was washed with brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was removed under reduced pressure
  13. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1-1/1)

Sources & evidence

ORD record
ord-48a1d4a708a547eaaa34c62f3f783dc2
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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