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Dicyclohexylcarbodiimide → HCID 178444291, Verbindung

HRID 370368
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 370368
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C@H:14]3[CH2:19][CH2:18][C@H:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:25]([C@H:28]1[CH2:33][CH2:32][C@H:31]([C:34](O)=[O:35])[CH2:30][CH2:29]1)[CH2:26][CH3:27].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:20]([C@H:17]1[CH2:18][CH2:19][C@H:14]([C:11]2[CH:12]=[CH:13][C:8]([C:5]3[CH:4]=[CH:3][C:2]([O:1][C:34]([C@H:31]4[CH2:32][CH2:33][C@H:28]([CH2:25][CH2:26][CH3:27])[CH2:29][CH2:30]4)=[O:35])=[CH:7][CH:6]=3)=[CH:9][CH:10]=2)[CH2:15][CH2:16]1)[CH2:21][CH2:22][CH2:23][CH3:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 178444287HCID 178444287, VerbindungHCID 178448101HCID 178448101, Verbindung

Produkt 1

HCID 178444291HCID 178444291, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

0.40 g of 4-hydroxy-4'-(trans-4-pentylcyclohexyl)biphenyl, 0.21 g of trans-4-propylcyclohexanecarboxylic acid and 0.025 g of (4-dimethylamino)pyridine were dissolved in 25 ml of dichloromethane and then 0.31 g of N,N'-dicyclohexylcarbodiimide was added portionwise within 10 minutes while stirring. The mixture was left to stand at room temperature for 3 days and then the precipitate was filtered off. The filtrate was diluted with dichloromethane, washed twice with 20 ml of saturated sodium bicarbonate solution each time and then with water, dried over sodium sulphate and concentrated. The crude trans-4-propylcyclohexanecarboxylic acid 4'-(trans-4-pentylcyclohexyl)-4-biphenylyl ester obtained was chromatographed on silica gel with hexane/dioxane (volume ratio 19:1). The fractions which were pure according to thin-layer chromatography were pooled and recrystallized from ethyl acetate. Yield 0.33 g; m.p. (C-S) 92° C., cl.p. (N-I) 319° C.; further phase transitions: S-S 154° C., S-S 218.5° C., S-N 240° C.

Aufarbeitung

  1. waitThe mixture was left
  2. filtrationthe precipitate was filtered off
  3. additionThe filtrate was diluted with dichloromethane
  4. washwashed twice with 20 ml of saturated sodium bicarbonate solution each time
  5. dry with materialwith water, dried over sodium sulphate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-41d3b56709164df594885a18414facfe
Quelldatensatz
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04526704

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