Hydrochloric Acid → 6-Nitro-1-benzofuran-2-carboxylic acid

HRID 15447

반응식

HRID 15447 반응식
[OH:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]([O:23]C)=[O:22].[OH-].[K+].Cl>O.C1COCC1>[N+:10]([C:8]1[CH:7]=[CH:6][C:3]2[CH:4]=[C:20]([C:21]([OH:23])=[O:22])[O:1][C:2]=2[CH:9]=1)([O-:12])=[O:11]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 755702-Hydroxy-4-nitrobenzaldehyde

생성물 1

HCID 131907266-Nitro-1-benzofuran-2-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
130 °C

실험 절차

5.8 g (34.7 mmol) of 2-hydroxy-4-nitrobenzaldehyde, 1.28 g (3.5 mmol) of tetra-N-butylammonium iodide and 19.2 g (138.8 mmol) of potassium carbonate are mixed, 7.9 g (72.9 mmol) of methyl chloroacetate are added and the mixture is heated at 130° C. for 12 h. 100 ml of THF and, with ice cooling, 11.7 g (208.2 mmol) of potassium hydroxide are added. Following the addition of 100 ml of water, the mixture is stirred at RT for 20 h. Using concentrated hydrochloric acid, the pH is adjusted to 0. The mixture is extracted with ethyl acetate. The organic phase is washed with water and dried over sodium sulfate. Following the addition of silica gel, the mixture is concentrated and chromatographed on silica gel (mobile phase gradient: toluene to toluene/methanol/glacial acetic acid 35:5:1). Concentration of the product fractions and drying under reduced pressure gives 1.31 g (18.2% of theory) of the title compound.

후처리

  1. extractionThe mixture is extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. additionthe addition of silica gel
  5. concentrationthe mixture is concentrated
  6. customchromatographed on silica gel (mobile phase gradient: toluene to toluene/methanol/glacial acetic acid 35:5:1)
  7. customConcentration of the product fractions and drying under reduced pressure

출처 및 근거

ORD 기록
ord-da39cad4635146c198633f65f2ac89a7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732477B2

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