Ethyl Acetate → [4-(Tetradecyloxy)phenyl methyl]aminobenzenemethanol

HRID 483563

Reaktionsgleichung

Reaktionsgleichung von HRID 483563
OC[C:3]1[CH:4]=[C:5]([NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:39](OCC)(=[O:41])C.[OH-].[Na+]>O1CCCC1.CCOCC>[CH2:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][NH:9][C:5]2[CH:4]=[CH:3][CH:8]=[CH:7][C:6]=2[CH2:39][OH:41])=[CH:16][CH:15]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 10003333N-[3-(Hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamideHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 86745365[4-(Tetradecyloxy)phenyl methyl]aminobenzenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the N-[3-(hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamide in 80 ml of tetrahydrofuran at 0° C. under argon is added 36.39 ml of 1M lithium aluminum hydride. Stirred at room temperature for 1 hour and refluxed for 7 hours. After stirring overnight and cooling to 0° C., ethyl acetate is added followed by sodium hydroxide solution until a solid forms. The mixture is diluted with ether, filtered and evaporated to a residue which is crystallized from hexane to give 6.7 g of the desired product as a white solid, m.p. 72°-75° C.

Aufarbeitung

  1. temperaturerefluxed for 7 hours
  2. stirringAfter stirring overnight
  3. temperaturecooling to 0° C.
  4. filtrationfiltered
  5. customevaporated to a residue which
  6. customis crystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-4dd33a4c6830456d8008f608b21ca243
Quelldatensatz
uspto-grants-1993_07
Patentnummer
US05225425

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