Acetic Acid → 4'-(12-Acetyloxydodecyloxy)biphenyl-4-carboxylic acid ethyl ester

HRID 2072643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2072643
O.O.O.O.O.[OH-].C[N+](C)(C)C.CN(C=O)C.[C:17]([OH:20])(=[O:19])[CH3:18].[CH2:21]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50]Br)=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=[O:25])[CH3:22]>CCOCC>[CH2:21]([O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][O:20][C:17](=[O:19])[CH3:18])=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)=[O:25])[CH3:22]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 82620Tetramethylammonium Hydroxide PentahydrateHCID 539084014'-(12-Bromododecyloxy)biphenyl-4-carboxylic acid ethyl ester

Produkt 1

HCID 536569284'-(12-Acetyloxydodecyloxy)biphenyl-4-carboxylic acid ethyl esterAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

60 m moles (10.9 g) of tetramethylammonium hydroxide pentahydrate was added to a DMF solution of 60 m moles (3.6 g) of acetic acid, and stirred for one hour, then 50 m moles (24.5 g) of the above 4'-(12-bromododecyloxy)biphenyl-4-carboxylic acid ethyl ester was added thereto, and stirred for 12 hours. After the reaction, the reaction solution was ether extracted. The extrate was concentrated, and then purified by column chromatography, to obtain 15.7 g of 4'-(12-acetyloxydodecyloxy)biphenyl-4-carboxylic acid ethyl ester [m.p. 80.1°-81.5° C⟧ (yield: 67%)

Aufarbeitung

  1. stirringstirred for 12 hours
  2. customAfter the reaction
  3. extractionextracted
  4. concentrationThe extrate was concentrated
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b42c5f380ae94eae935561878762c4d5
Quelldatensatz
uspto-grants-1990_04
Patentnummer
US04913839

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