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

HRID 66930

Reaktionsgleichung

Reaktionsgleichung von HRID 66930
[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][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:27])[CH2:25]O.O1CCCC1>CS(O)(=O)=O.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][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[CH:10][CH:11]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 8254Dimethyl EtherHCID 927424,4'-Bis(dimethylamino)benzhydrolHCID 561337Benzyl 2-hydroxyacetate

Produkt 1

HCID 131712798Bis(p-dimethylaminophenyl)Methoxy Acetic Acid, Benzyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6395Methanesulfonic AcidKatalysatorHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 4,4'-bis(N,N-dimethylamino)benzhydrol, methyl ether (11.0 g, 0.039 mole), benzyl glycolate (6.6 g, 0.039 mole), 90 ml of tetrahydrofuran, 200 ml of hexane, and 10 drops of methanesulfonic acid was refluxed for 6 hours, replacing solvent as distillate was removed; then, 10 drops of tetramethylguanidine was added to discharge the color and the reaction mixture was filtered hot and cooled. A white solid formed which was filtered, washed with petroleum ether and then recrystallized from 4/1 hexane/acetone. The resulting white crystalline product had a mp 101.8°-103° C.

Aufarbeitung

  1. customwas removed
  2. additionthen, 10 drops of tetramethylguanidine was added
  3. filtrationthe reaction mixture was filtered hot
  4. temperaturecooled
  5. customA white solid formed which
  6. filtrationwas filtered
  7. washwashed with petroleum ether
  8. customrecrystallized from 4/1 hexane/acetone

Quellen und Nachweise

ORD-Eintrag
ord-c8c7ee5975cb486097236de1755ecc83
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04343939

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