Water → 2'-Carboxymethoxy-6'-hydroxy-3-(2-hydroxyethoxy)dihydrochalcone

HRID 230894Notes

Reaction equation

HRID 230894 reaction equation
[OH:1][C:2]1[C:7]([C:8](=[O:10])[CH3:9])=[C:6]([O:11][CH2:12][C:13]([O:15]C)=[O:14])[CH:5]=[CH:4][CH:3]=1.[OH:17][CH2:18][CH2:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O.O.[OH-].[K+]>C(O)C.[C].[Pd]>[C:13]([CH2:12][O:11][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([OH:1])[C:7]=1[C:8](=[O:10])[CH:9]=[CH:24][CH:23]1[CH:26]=[CH:27][CH:28]=[C:21]([O:20][CH2:19][CH2:18][OH:17])[CH2:22]1)([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 6453965Benzaldehyde, 3-(2-hydroxyethoxy)-HCID 105370846'-Hydroxy-2'-(methoxycarbonylmethoxy)acetophenone

Product 1

HCID 671358072'-Carboxymethoxy-6'-hydroxy-3-(2-hydroxyethoxy)dihydrochalconeYield 99.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 6′-hydroxy-2′-(methoxycarbonylmethoxy)acetophenone (1 g) and 3-(2-hydroxyethoxy)benzaldehyde (0.74 g) in ethanol (12 mL) were added water (3 mL) and potassium hydroxide (3 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 10% palladium-carbon powder (0.2 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 8 hours. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was dissolved in water, and the solution was washed with diethyl ether. The aqueous layer was acidified by addition of concentrated hydrochloric acid, and the resulting mixture was extracted with ethyl acetate twice. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was treated with diethyl ether, and the precipitated crystals were collected by filtration. The crystals were dried under reduced pressure to give the title compound (1.6 g).

Workup

  1. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere for 8 hours
  2. customThe insoluble material was removed by filtration
  3. customthe solvent of the filtrate was removed under reduced pressure
  4. dissolutionThe residue was dissolved in water
  5. washthe solution was washed with diethyl ether
  6. additionThe aqueous layer was acidified by addition of concentrated hydrochloric acid
  7. extractionthe resulting mixture was extracted with ethyl acetate twice
  8. washThe extract was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was removed under reduced pressure
  11. additionThe residue was treated with diethyl ether
  12. filtrationthe precipitated crystals were collected by filtration
  13. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-78b6c384e39f49b6bba136e99252fe37
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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