Dimethyl Sulfoxide → 3-(2-Methoxyphenyl)propanal

HRID 743385

Reaktionsgleichung

Reaktionsgleichung von HRID 743385
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH2:20][CH2:21][OH:22].C(N(CC)CC)C>C(Cl)Cl>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][CH2:20][CH:21]=[O:22]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2549583-(2-Methoxy-phenyl)-propan-1-ol

Produkt 1

HCID 2667443-(2-Methoxyphenyl)propanalAusbeute 85,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

Meanwhile, a solution of 760 mg of dimethyl sulfoxide in 2 ml of methylene chloride was added dropwise to a solution of 740 mg of oxalyl chloride in 12 ml of methylene chloride at -60° C., with stirring, and the mixture was stirred at the same temperature for 10 minutes. At the end of this time, a solution of 640 mg of 3-(2-methoxyphenyl)propanol (prepared as described above) in 3 ml of methylene chloride was added dropwise to the mixture, and the mixture was stirred for a further 10 minutes. 1.96 g of triethylamine were then slowly added dropwise to the mixture at the same temperature. The cooling bath was removed, and the reaction mixture was stirred at room temperature for 30 minutes and then mixed with water. The methylene chloride layer was separated, dried over anhydrous magesium sulfate, and concentrated by evaporation under reduced pressure. The oily residue thus obtained was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 540 mg of 3-(2-methoxyphenyl)propanal as a colorless oil.

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 10 minutes
  2. stirringthe mixture was stirred for a further 10 minutes
  3. customThe cooling bath was removed
  4. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  5. additionmixed with water
  6. customThe methylene chloride layer was separated
  7. dry with materialdried over anhydrous magesium sulfate
  8. concentrationconcentrated by evaporation under reduced pressure
  9. customThe oily residue thus obtained
  10. customwas purified by column chromatography through silica gel
  11. additionby volume mixture of hexane and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-423537483d614a00b9cff9a52b531afa
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556864

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