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Acetone → Methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate

HRID 899561
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 899561
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH2:6][CH:5]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:27](=O)([O-])[O-:28].[K+].[K+].CC(C)=O>CO>[CH2:19]([O:8][C:9]1[CH:10]=[CH:11][C:2]([CH3:1])=[CH:3][C:4]=1[CH:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:6][C:7]([O:28][CH3:27])=[O:12])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 37916436-Methyl-4-phenyl-3,4-dihydrochromen-2-one

Produkt 1

HCID 11667650Methyl 3-(2-benzyloxy-5-methylphenyl)-3-phenylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Versuchsvorschrift

675 g of 6-methyl-4 phenyl-3,4-dihydrocoumarin, 372 ml of benzyl bromide, and 513 g of potassium carbonate were charged into a round bottom flask containing a mixture of 2025 ml of acetone and 2025 ml of methanol. The contents were heated to reflux temperature for about 2-3 hours. Distilled off the solvent from the reaction mass at atmospheric conditions below 75° C. then under vacuum (about 600 mm Hg) at below 85° C. 6750 ml of water was added to the residue and stirred for 15 minutes for dissolution. Extracted the solution twice with ethyl acetate (4000 ml). Combined organic layers were washed with water (2×3375 ml) and distilled the solvent under vacuum (about 600 mm Hg) at below 85° C. 2025 ml of methanol was added to the residue at 50-55° C., then stirred the solution at 0-5° C. for about 2 hours. Filtered the formed solid and washed with 675 ml of methanol. Dried the solid at 50-55° C. for about 2-3 hours under vacuum (about 600 mm/Hg) to get 850 g of the title compound.

Aufarbeitung

  1. additioncontaining
  2. temperatureThe contents were heated
  3. temperatureto reflux temperature for about 2-3 hours
  4. distillationDistilled off the solvent from the reaction mass at atmospheric conditions below 75° C.
  5. customat below 85° C
  6. addition6750 ml of water was added to the residue
  7. extractionExtracted the solution twice with ethyl acetate (4000 ml)
  8. washCombined organic layers were washed with water (2×3375 ml)
  9. distillationdistilled the solvent under vacuum (about 600 mm Hg) at below 85° C
  10. addition2025 ml of methanol was added to the residue at 50-55° C.
  11. stirringstirred the solution at 0-5° C. for about 2 hours
  12. filtrationFiltered the formed solid
  13. washwashed with 675 ml of methanol
  14. customDried the solid at 50-55° C. for about 2-3 hours under vacuum (about 600 mm/Hg)

Quellen und Nachweise

ORD-Eintrag
ord-6c15330114f94bd189d9ec9a3e228372
Quelldatensatz
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07355077B2

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