Hydrochloric Acid → 6-Hydroxy-3-coumaranone

HRID 2118095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2118095
C[O-].[Na+].Cl[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[OH:15])=[O:7].Cl>CO>[OH:14][C:11]1[CH:12]=[CH:13][C:8]2[C:6](=[O:7])[CH2:5][O:15][C:9]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 23846862-Chloro-1-(2,4-dihydroxyphenyl)ethan-1-oneHCID 10942334Sodium Methoxide

Produkt 1

HCID 2357176-Hydroxy-3-coumaranone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Solid NaOMe (6134 g) was added to a 0° C. solution of the chloroketone 2 (7062 g) in 49 L of methanol (MeOH) in portions over 2 h while maintaining the temperature at <20° C. The slurry was aged at room temperature for 1 h, at which time cyclization was determined to be complete by HPLC. The mixture was cooled to 0° C., and 2N HCl (49 L) was added while maintaining the temperature at <20° C. The slurry was cooled to 5-10° C., filtered, and washed first with cold 1:1 MeOH/water (5 L), and then with water (16 L). The wet filter cake was slurry washed with isopropyl alcohol (IPA) (18 L), and then was finally washed with heptane. The filter cake was then dried under a fast stream of nitrogen. Ketone 3 was isolated as a white solid.

Aufarbeitung

  1. temperaturewhile maintaining the temperature at <20° C
  2. temperaturewhile maintaining the temperature at <20° C
  3. temperatureThe slurry was cooled to 5-10° C.
  4. filtrationfiltered
  5. washwashed first with cold 1:1 MeOH/water (5 L)
  6. washwashed with isopropyl alcohol (IPA) (18 L)
  7. washwas finally washed with heptane
  8. customThe filter cake was then dried under a fast stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-52d432d4fb35432da86c56c5b1dfe762
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442808B2

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