Acetic Acid → 4'-Chloro-2-methoxychalcone

HRID 1478237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1478237
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][CH:5]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.CC(O)=O>CO>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])/[CH:11]=[CH:17]/[C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[O:14][CH3:13])=[CH:6][CH:5]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 7467P-ChloroacetophenoneHCID 86582-MethoxybenzaldehydeHCID 14797Potassium Hydroxide

Produkt 1

HCID 53462324'-Chloro-2-methoxychalconeAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

KOH (1.415 g, 25.2 mmol) was added to a solution of 1-(4-chlorophenyl)ethanone (3.9 g, 25.2 mmol) and 2-methoxybenzaldehyde (3.43 g, 25.2 mmol) in methanol (100 ml) at RT and the solution was stirred for 18 hours. The solution was concentrated under reduced pressure until a precipitate was formed. AcOH (1.444 ml, 25.2 mmol) was added and the mixture was cooled down to 0° C.-5° C. The mixture was stirred for 1 hour and the light yellow precipitate was separated by filtration and washed with cold methanol to afford 6.72 g (24.39 mmol, 97% yield) of the title compound. LCMS: (M+H)=273; tR=1.28 min (LC-MS 3). 1H-NMR (d6-DMSO, 600 MHz) δ ppm 8.12 (d, 2H) 8.04 (d, 1H) 7.98 (d, 1H) 7.86 (d, 1H) 7.62 (d, 2H) 7.45 (t, 1H) 7.10 (d, 1H) 7.02 (t, 1H) 3.88 (s, 3H).

Aufarbeitung

  1. concentrationThe solution was concentrated under reduced pressure until a precipitate
  2. customwas formed
  3. temperaturethe mixture was cooled down to 0° C.-5° C
  4. stirringThe mixture was stirred for 1 hour
  5. customthe light yellow precipitate was separated by filtration
  6. washwashed with cold methanol

Quellen und Nachweise

ORD-Eintrag
ord-fada9e3626de4864b3bcbec64f9fd4c3
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403827B2

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