Iodine → Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

HRID 358288

반응식

HRID 358288 반응식
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[Na+].[I-:13].OS(O)(=O)=O.II>[OH-].[Na+]>[I:13][C:10]1[C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=[C:3]([CH:11]=1)[CH:2]=[O:1]

참가 물질

6

반응물 4

HCID 807IodineHCID 1118Sulfuric Acid2회HCID 1183VanillinHCID 5238Sodium Iodide

생성물 1

HCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-수율 99%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
90 °C

실험 절차

Vanillin (28.4 g, 200 mmole (millimole)) was dissolved in 1N NaOH (200 ml) and warmed to 90° C. to avoid precipitation of sodium vanillate. A 2 molar aqueous solution of NaI3.NaI (105 ml, 210 mmole I2) plus 3.55 molar aqueous H2SO4 (5 ml) was added over 3 hours with stirring. The iodine color was discharged, and a pale tan stirrable precipitate formed. The solution was then cooled to room temperature, acidified to pH 2-3 with 20% aqueous H2SO4, and extracted with 10% methanol/90% chloroform. The organic phase was dried (MgSO4) and the solvent stripped to yield 53 g (99%) of 5-iodovanillin, more than 95% pure as analyzed by nuclear magnetic resonance spectroscopy (NMR).

후처리

  1. customprecipitation of sodium vanillate
  2. customa pale tan stirrable precipitate formed
  3. temperatureThe solution was then cooled to room temperature
  4. extractionextracted with 10% methanol/90% chloroform
  5. dry with materialThe organic phase was dried (MgSO4)

출처 및 근거

ORD 기록
ord-b93f7d28983548e283afb2b789cd9b20
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04465864

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