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

HRID 358288

反応式

HRID 358288 の反応式
[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]

参加物

6

反応物 4

HCID 807IodineHCID 1118Sulfuric Acid2 回HCID 1183VanillinHCID 5238Sodium Iodide

生成物 1

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

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b93f7d28983548e283afb2b789cd9b20
出典データセット
uspto-grants-1984_08
特許番号
US04465864

関連ノート

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