Dicyclohexylcarbodiimide → 4'-Hexylbiphenyl-4-yl 1-cyano-3-methylcyclohex-anecarboxylate

HRID 231460

Reaktionsgleichung

Reaktionsgleichung von HRID 231460
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([C:18]1([C:25]([OH:27])=[O:26])[CH2:23][CH2:22][CH2:21][CH:20]([CH3:24])[CH2:19]1)#[N:17].[CH2:28]([C:34]1[CH:39]=[CH:38][C:37]([C:40]2[CH:45]=[CH:44][C:43](O)=[CH:42][CH:41]=2)=[CH:36][CH:35]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C(N(CC)C1C=CN=CC=1)C>C(Cl)Cl>[C:16]([C:18]1([C:25]([O:27][C:43]2[CH:44]=[CH:45][C:40]([C:37]3[CH:36]=[CH:35][C:34]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:39][CH:38]=3)=[CH:41][CH:42]=2)=[O:26])[CH2:23][CH2:22][CH2:21][CH:20]([CH3:24])[CH2:19]1)#[N:17]

Komponenten

6

Edukt 4

HCID 10868DicyclohexylcarbodiimideHCID 117687514-DiethylaminopyridineHCID 135748604'-Hexyl-biphenyl-4-olHCID 198007731-Cyano-3-methylcyclohexane-1-carboxylic acid

Produkt 1

HCID 198007614'-Hexylbiphenyl-4-yl 1-cyano-3-methylcyclohex-anecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 23 g of dicyclohexylcarbodiimide in 50 ml of CH2Cl2 is added at room temperature to a mixture of 16 g of 1-cyano-3-methyl-cyclohexanecarboxylic acid, 25 g of 4'-hexylbiphenyl-4-ol, 1.2 g of 4-diethylaminopyridine and 200 ml of methylene chloride, and the mixture is stirred for 2 hours. Customary working up and separation by column chromatography (silica gel/toluene) and recrystallization gives the pure product 4'-hexylbiphenyl-4-yl 1-cyano-3-methylcyclohex-anecarboxylate, m.p. 51°.

Aufarbeitung

  1. customseparation
  2. customby column chromatography (silica gel/toluene) and recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-654df5f5c24c4203a7fcaa89aacdf3b9
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04846998

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