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Tetrahydrofuran → Bis(p-dimethylaminophenyl)Methoxy Acetic Acid, Ethyl Ester

HRID 66926
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Reaktionsgleichung

Reaktionsgleichung von HRID 66926
[CH3:1][N:2]([C:4]1[CH:20]=[CH:19][C:7]([CH:8]([OH:18])[C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)[CH3:3].COC.[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH2:25]O.O1CCCC1>CS(O)(=O)=O.CN(C)C(=N)N(C)C.CCCCCC>[CH3:17][N:15]([CH3:16])[C:12]1[CH:13]=[CH:14][C:9]([CH:8]([C:7]2[CH:19]=[CH:20][C:4]([N:2]([CH3:1])[CH3:3])=[CH:5][CH:6]=2)[O:18][CH2:25][C:24]([O:28][CH2:29][CH3:30])=[O:27])=[CH:10][CH:11]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 8254Dimethyl EtherHCID 12184Ethyl GlycolateHCID 927424,4'-Bis(dimethylamino)benzhydrol

Produkt 1

HCID 131712796Bis(p-dimethylaminophenyl)Methoxy Acetic Acid, Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6395
Methanesulfonic Acid
Katalysator
HCID 664601,1,3,3-TetramethylguanidineKatalysator
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (11.0 g, 0.039 mole), ethyl glycolate 4.04 g, 0.039 mole), 70 ml of tetrahydrofuran, 230 ml of n-hexane and one drop of methanesulfonic acid was refluxed for 2 hours. On completion of the reaction, 2 drops of tetramethylguanidine was added to discharge the blue color. The reaction mixture was filtered hot and the filtrate was cooled. An oily layer formed which was removed and stripped free of solvent; the remaining filtrate was also stripped, leaving an oil. Both samples of oil were combined and chilled. A waxy solid formed which, on repeated trituration with petroleum ether, gave a white solid. Recrystallization from a mixture of petroleum ether/acetone gave a white solid, mp 63°-67.5° C.

Aufarbeitung

  1. additionwas added
  2. filtrationThe reaction mixture was filtered hot
  3. temperaturethe filtrate was cooled
  4. customAn oily layer formed which
  5. customwas removed
  6. customleaving an oil
  7. temperaturechilled
  8. customA waxy solid formed which
  9. customgave a white solid
  10. customRecrystallization
  11. additionfrom a mixture of petroleum ether/acetone
  12. customgave a white solid, mp 63°-67.5° C.

Quellen und Nachweise

ORD-Eintrag
ord-aa0214dade6640c69e0700ce2b97d467
Quelldatensatz
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04343939

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