1-Allyl-2,3,4,5-tetramethoxy-6-methylbenzene → 2-(2,3,4,5-Tetramethoxy-6-methylphenyl)acetaldehyde

HRID 1742491ノート

反応式

HRID 1742491 の反応式
[CH2:1]([C:4]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[C:7]([O:13][CH3:14])=[C:6]([O:15][CH3:16])[C:5]=1[O:17][CH3:18])[CH:2]=C.I([O-])(=O)(=O)=[O:20].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:18][O:17][C:5]1[C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[C:8]([O:11][CH3:12])=[C:9]([CH3:10])[C:4]=1[CH2:1][CH:2]=[O:20]

参加物

6

反応物 2

HCID 125607701-Allyl-2,3,4,5-tetramethoxy-6-methylbenzeneHCID 23667635Sodium periodate

生成物 1

HCID 190092572-(2,3,4,5-Tetramethoxy-6-methylphenyl)acetaldehyde

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

109 mg of osmium tetroxide were added to a solution of 7.98 of 1-allyl-2,3,4,5-tetramethoxy-6-methylbenzene [prepared as described in step (a) above] in a mixture of 300 ml of dioxane and 100 ml of water, and the resulting mixture was stirred at room temperature for 10 minutes. An aqueous solution of 35.6 g of sodium periodate was then added dropwise, and the mixture was stirred at room temperature for 2 hours. At the end of this time, the reaction mixture was freed from the dioxane by evaporation under reduced pressure, and the resulting concentrate was poured into a saturated aqueous solution of sodium chloride, after which it was extracted with diisopropyl ether. The solvent was then removed from the extract by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a gradient elution method with mixtures of hexane and ethyl acetate ranging from 8:1 to 5:1 by volume as the eluent, to give 4.64 g of the title compound.

後処理

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customAt the end of this time, the reaction mixture was freed from the dioxane by evaporation under reduced pressure
  3. concentrationthe resulting concentrate
  4. additionwas poured into a saturated aqueous solution of sodium chloride
  5. extractionafter which it was extracted with diisopropyl ether
  6. customThe solvent was then removed from the
  7. extractionextract by distillation under reduced pressure
  8. customthe resulting residue was purified by column chromatography through silica gel
  9. washa gradient elution method with mixtures of hexane and ethyl acetate ranging from 8:1 to 5:1 by volume as the eluent

出典と根拠

ORDレコード
ord-041d8bca49b640d18d8c30faf2dea9f1
出典データセット
uspto-grants-1994_08
特許番号
US05338855

反応ノート

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