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Sulfuric Acid → 2-(2-Isobutoxyphenyl)ethanal

HRID 2249680
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HRID 2249680 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

11

반응물 5

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

생성물 1

HCID 178165132-(2-Isobutoxyphenyl)ethanal수율 64.9%

시약·촉매·용매 5

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매2회HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-759bc34be1f5479fa00c690c5c8b725e
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07314888B1

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