Benzyl Chloride → 3-Benzyloxy-2-ethyl-4-pyrone

HRID 1656932

Reaktionsgleichung

Reaktionsgleichung von HRID 1656932
[CH2:1]([C:3]1[O:4][CH:5]=[CH:6][C:7](=[O:10])[C:8]=1[OH:9])[CH3:2].[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO.O.C(OCC)C>[CH2:13]([O:9][C:8]1[C:7](=[O:10])[CH:6]=[CH:5][O:4][C:3]=1[CH2:1][CH3:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 21059Ethyl Maltol

Produkt 1

HCID 105855423-Benzyloxy-2-ethyl-4-pyroneAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a stirred mixture of 2-ethyl-3-hydroxy-4-pyrone (49 g, 0.35 mol) in methanol (600 ml) and sodium hydroxide (16 g, 0.4 mol) dissolved in water (50 ml) was added benzyl chloride (47.2 ml, 0.41 mol) dropwise at room temperature. After heating under reflux for 48 hours the reaction mixture was cooled, filtered and the filtrate rotary evaporated to provide an oil. The oil was extracted with dichloromethane (300 ml), the solution washed with 5% w/v sodium hydroxide solution (3×250 ml) and water (3×250 ml), then dried over anhydrous sodium sulphate, filtered and rotary evaporated to provide an oil which was dissolved in diethyl ether and crystallized by coating with liquid nitrogen. Recrystallization from diethyl ether gave the title compound as colourless crystals (52.5 g, 65%), m.p. 33°-34° C.

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureunder reflux for 48 hours the reaction mixture
  3. temperaturewas cooled
  4. filtrationfiltered
  5. customthe filtrate rotary evaporated
  6. customto provide an oil
  7. extractionThe oil was extracted with dichloromethane (300 ml)
  8. washthe solution washed with 5% w/v sodium hydroxide solution (3×250 ml) and water (3×250 ml)
  9. dry with materialdried over anhydrous sodium sulphate
  10. filtrationfiltered
  11. customrotary evaporated
  12. customto provide an oil which
  13. customcrystallized by coating with liquid nitrogen
  14. customRecrystallization from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3937bd58a92f491693c6a75d5329f494
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256676

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