Water → HCID 67135916, 화합물

HRID 230904

반응식

HRID 230904 반응식
[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.[CH:17]([C:19]1[CH:29]=[CH:28][C:22]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1)=O.O.[OH-].[K+]>C(O)C.[C].[Pd]>[C:25]([CH2:24][CH2:23][C:22]1[CH:21]=[CH:20][CH:19]([CH:17]=[CH:9][C:8]([C:7]2[C:2]([OH:1])=[CH:3][CH:4]=[CH:5][C:6]=2[O:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])[CH2:29][CH:28]=1)([OH:27])=[O:26]

참가 물질

7

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 980772-Propenoic acid, 3-(4-formylphenyl)-HCID 105370846'-Hydroxy-2'-(methoxycarbonylmethoxy)acetophenone

생성물 1

HCID 67135916HCID 67135916, 화합물수율 93.3%

시약·촉매·용매 2

HCID 178418390HCID 178418390, 화합물촉매HCID 702Ethanol용매

실험 절차

To a suspension of 6′-hydroxy-2′-(methoxycarbonylmethoxy)acetophenone (1 g) and 4-formylcinnamic acid (0.79 g) in ethanol (10 mL) were added water (2 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 overnight. The insoluble material was removed by filtration. The solvent of the filtrate was removed under reduced pressure. To the residue was added 2 mol/L hydrochloric acid, and the precipitated crystals were collected by filtration. The crystals were washed with water and dried under reduced pressure to give 4-(2-carboxyethyl)-2′-(carboxymethoxy)-6′-hydroxydihydrochalcone (1.55 g). This material was dissolved in acetic acid (12 mL). To the solution were added sodium acetate (8.6 g) and acetic anhydride (8.6 mL), and the mixture was stirred at 115° C. overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water twice. To the extract was added 1 mol/L aqueous sodium hydroxide solution, and the aqueous layer was separated. The aqueous layer was acidified by addition of 2 mol/L hydrochloric acid, and the resulting mixture was extracted with diethylether. The extract was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1) to give the title compound (0.29 g).

후처리

  1. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere overnight
  2. customThe insoluble material was removed by filtration
  3. customThe solvent of the filtrate was removed under reduced pressure
  4. additionTo the residue was added 2 mol/L hydrochloric acid
  5. filtrationthe precipitated crystals were collected by filtration
  6. washThe crystals were washed with water
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-95499184f675458783b7f450c649666f
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566699B2

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