Benzyl Alcohol → 4-Benzyloxy-3-pyrrolin-2-one

HRID 1194086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1194086
[CH3:1][O:2][C:3]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]=1.C(O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CS(O)(=O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:2][C:3]1[CH2:7][NH:6][C:5](=[O:8])[CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 5747694-methoxy-2,5-dihydro-1H-pyrrol-2-one

Produkt 1

HCID 27247414-Benzyloxy-3-pyrrolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5.7 g (50 mmol) of 4-methoxy-3-pyrrolin-2-one and 10.8 g (100 mmol) of benzyl alcohol were mixed with 0.4 g (4 mmol) of methanesulfonic acid and stirred for 24 hours at 80° C. and 20 mbars. Then the reaction solution was mixed with 50 ml of ice water and 100 ml of methylene chloride, and neutralized with 4 ml of saturated NaHCO3 solution. The aqueous phase was extracted twice with 50 ml of methylene chloride each. After drying of the organic phase over Na2SO4 and distilling off of the solvent, the residue was mixed with 150 ml of ice water, heated to 100° C. and azeotropically distilled off with 100 ml of water-benzyl alcohol. The crystals precipitated during cooling were recrystallized hot from 50 ml of toluene. 6.7 g of white, crystalline product with a melting point of 147° to 148° C. was obtained:

Aufarbeitung

  1. extractionThe aqueous phase was extracted twice with 50 ml of methylene chloride each
  2. dry with materialAfter drying of the organic phase over Na2SO4
  3. distillationdistilling off of the solvent
  4. additionthe residue was mixed with 150 ml of ice water
  5. temperatureheated to 100° C.
  6. distillationazeotropically distilled off with 100 ml of water-benzyl alcohol
  7. customThe crystals precipitated
  8. temperatureduring cooling
  9. customwere recrystallized hot from 50 ml of toluene
  10. custom6.7 g of white, crystalline product with a melting point of 147° to 148° C. was obtained

Quellen und Nachweise

ORD-Eintrag
ord-f73774c33e924e729b0b90fb6a08e4fa
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04812578

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