Chloroacetone → HCID 13842858, Verbindung

HRID 263953

Reaktionsgleichung

Reaktionsgleichung von HRID 263953
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4](=[O:12])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21](=[O:23])[CH3:22]>CC(C)=O>[O:23]=[C:21]([CH3:22])[CH2:20][O:1][C:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:5][C:4](=[O:12])[CH:3]=1

Komponenten

5

Edukt 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 546829304-Hydroxycoumarin

Produkt 1

HCID 13842858HCID 13842858, VerbindungAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxycoumarin (1.62 g, 10 mmol) in acetone (20 ml) were added potassium carbonate (5.53 g, 40 mmol) and chloroacetone (1.38 g, 15 mmol). The resulting mixture was refluxed for 4 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 4-(2-Oxopropoxy)-2H-1-benzopyran-2-one (1a) (1.28 g, 55.1%) as a white needle crystal. mp: 163°-165° C.; IR(KBr) νmax : 1716, 1625; UV(CHCl3) λmax (log ε): 305 (3.83), 266 (4.05); 1H-NMR (CDCl3): δ2.36 (s, 3H, CH3), 4.77 (s, 2H, OCH2), 5.57 (s, 1H, 3-H), 7.28-7.36 (m, 2H, 6- and 8-H), 7.54-7.63 (m, 1H, 7-H), 7.88-7.94 (m, 1H, 5-H). Anal. Calcd for C12H10O4 : C, 66.05; H, 4.62. Found: C, 66.01; H, 4.64.

Aufarbeitung

  1. temperatureThe resulting mixture was refluxed for 4 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-c0ed30072ce54a9c994fe858bd3b9428
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646164

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