Phenacyl bromide → 7-(2-oxo-2-phenylethoxy)-2H-chromen-2-one

HRID 263959

Reaktionsgleichung

Reaktionsgleichung von HRID 263959
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:16]=[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8](=[O:12])[O:9][C:10]=2[CH:11]=1

Komponenten

5

Edukt 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 5281426Umbelliferone

Produkt 1

HCID 8543337-(2-oxo-2-phenylethoxy)-2H-chromen-2-oneAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 7-hydroxycoumarin (1.62 g, 10 mmol) in acetone (60 ml) were added 2-bromoacetophenone (1.99 g, 10 mmol) and potassium carbonate (5.53 g, 40 mmol). The mixture was refluxed for 3 h. (monitored by TLC). Evaporation of the solvent gave a residue which was poured into ice water (50 ml). The resulting solid was collected and crystallized from ethyl acetate to afford 7-(2-oxo-2-phenylethoxy)-2H-1-benzopyran-2-one (4a) (1.53 g, 73.1%) as a needle crystal. mp: 163°-165° C.; IR(KBr) νmax : 1728, 1702, 1627; UV(CHCl3) λmax (log ε): 320 (4.16), 249 (4.13); 1H-NMR (CDCl3): δ5.39 (s, 2H, OCH2), 6.27 (d, 1H, 3-H), 6.80 (d, 1H, 8-H), 6.93 (dd, 1H, 6-H), 7.40 (d, 1H, 5-H), 7.49-7.68 (m, 4H, 4-H and aromatic H). Anal Calcd for C17H12O4 : C, 72.85; H, 4.32. Found: C, 72.98; H, 4.35.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 3 h. (monitored by TLC)
  2. customEvaporation of the solvent
  3. customgave a residue which
  4. customThe resulting solid was collected
  5. customcrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-9398a07558da47758352b8b805903ead
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646164

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