Sodium Hydroxide → HCID 57911671, 화합물

HRID 1158459

반응식

HRID 1158459 반응식
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12]C)=[CH:6][C:3]=1[CH:4]=[O:5].[OH-].[Na+].CCCCCC.CCOC(C)=O>OS(O)(=O)=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[CH:6][C:3]=1[CH:4]=[O:5]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 2793512-Chloro-4,5-dimethoxybenzaldehydeHCID 21226206Ethyl acetate hexane

생성물 1

HCID 57911671HCID 57911671, 화합물

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
65 °C

실험 절차

2-Chloro-4,5-dimethoxybenzaldehyde (5.00 g, 24.9 mmol; commercially available from Akos Consulting) is dissolved at room temperature in conc. H2SO4 (23 mL; Riedel) at room temperature. The deeply colored mixture is heated at 65° C. overnight with stirring, and after cooling is poured with caution into ice-water containing 38 g of solid NaOH (pH 14). The water phase is washed twice with AcOEt, and then is adjusted to pH 1 by addition of HCl 37% with ice-cooling to form a white suspension. Extraction with AcOEt, drying of the organics over MgSO4 and evaporation gives the crude product in a mixture with unreacted starting material. The title compound is obtained after silica gel chromatography (hexane/AcOEt gradient from 3:1 to 1:1) as white solid. TLC, Rf (hexane/AcOEt 1:1)=0.35. MS: 187.0 [M+H]+. ]+. 1H-NMR (DMSO-d6): δ 3.41 (s, 3H), 7.14 (s, 1H), 7.45 (s, 1H), 9.83 (s, 1H), 10.2 (s, 1H) ppm.

후처리

  1. temperatureafter cooling
  2. washThe water phase is washed twice with AcOEt
  3. additionis adjusted to pH 1 by addition of HCl 37% with ice-
  4. temperaturecooling
  5. customto form a white suspension
  6. extractionExtraction with AcOEt
  7. customdrying of the
  8. customorganics over MgSO4 and evaporation
  9. customgives the crude product in a mixture

출처 및 근거

ORD 기록
ord-d128e6b819514f98b801f69f1dfdd085
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807709B2

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