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Sulfuric Acid → 2-(2-Isobutoxyphenyl)ethanal

HRID 2249680
ノート
印刷プレビュー

反応式

HRID 2249680 の反応式
[Cl-].[CH3:2][O:3]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(NC(C)C)(C)C.C([Li])CCC.[CH2:36]([O:40][C:41]1[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=1[CH:43]=O)[CH:37]([CH3:39])[CH3:38].S(=O)(=O)(O)O>O1CCCC1.CCCCCC.O.C(OCC)(=O)C.O1CCOCC1>[CH2:36]([O:40][C:41]1[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=1[CH2:43][CH:2]=[O:3])[CH:37]([CH3:39])[CH3:38]
参加物実験手順後処理出典と根拠反応ノート

参加物

11

反応物 5

HCID 1118Sulfuric AcidHCID 7912DiisopropylamineHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 38575282-(2-Methylpropoxy)benzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 178165132-(2-Isobutoxyphenyl)ethanal収率 64.9%

試薬・触媒・溶媒 5

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

In 200 ml of tetrahydrofuran are suspended 144 g of (methoxymethyl)triphenylphosphonium chloride and 43 g of diisopropylamine, to which is dropwise added 253 ml of a 1.6 mol/L solution of n-butyllithium in hexane at −50° C. over a period of one hour. The mixture thus obtained is stirred at ambient temperature for one hour. Then, a solution of 25 g of 2-isobutoxy-benzaldehyde in 100 ml of tetrahydrofuran is dropwise added to the reaction mixture obtained above at −50° C. over a period of one hour, and the mixture thus obtained is stirred at ambient temperature for one hour. The reaction mixture is added to a mixture of ethyl acetate and water, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue obtained above is mixed with 260 ml of 5% aqueous solution of sulfuric acid and 100 ml of dioxane, heated under reflux for 2 hours, cooled to ambient temperature and diluted with 500 ml of water. Ethyl acetate is added to the reaction mixture and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=95:5) to obtain 17.5 g of 2-(2-isobutoxyphenyl)ethanal as a colorless oily product.

後処理

  1. customat −50° C.
  2. customof one hour
  3. customThe mixture thus obtained
  4. customobtained above at −50° C. over a period of one hour
  5. customthe mixture thus obtained
  6. stirringis stirred at ambient temperature for one hour
  7. customthe organic layer is separated
  8. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationthe solvent is distilled off under reduced pressure
  11. customThe residue obtained
  12. temperatureheated
  13. temperatureunder reflux for 2 hours
  14. temperaturecooled to ambient temperature
  15. customthe organic layer is separated
  16. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  17. dry with materialdried over anhydrous magnesium sulfate
  18. distillationthe solvent is distilled off under reduced pressure
  19. customThe residue thus obtained
  20. customis purified by silica gel column chromatography (eluent; hexane:ethyl acetate=95:5)

出典と根拠

ORDレコード
ord-759bc34be1f5479fa00c690c5c8b725e
出典データセット
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07314888B1

反応ノート

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