2-(3,4,5-Tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenone → 9-(4-Chlorophenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenol

HRID 1047401Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1047401
[CH2:1]([O:19][CH:20]1[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23][CH:22]([CH2:64][O:65][C:66]2[CH:78]=[CH:77][C:76]3[C:75]4[C:70](=[CH:71][CH:72]=[CH:73][CH:74]=4)[C:69](=[O:79])[C:68]=3[CH:67]=2)[CH2:21]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Cl:80][C:81]1[CH:86]=[CH:85][C:84]([Mg]Br)=[CH:83][CH:82]=1>C1COCC1>[Cl:80][C:81]1[CH:86]=[CH:85][C:84]([C:69]2([OH:79])[C:68]3[CH:67]=[C:66]([O:65][CH2:64][CH:22]4[CH2:21][CH:20]([O:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:25]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH:24]([O:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[CH2:23]4)[CH:78]=[CH:77][C:76]=3[C:75]3[C:70]2=[CH:71][CH:72]=[CH:73][CH:74]=3)=[CH:83][CH:82]=1

Komponenten

4

Edukt 2

HCID 594992172-(3,4,5-Tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenoneHCID 178478191HCID 178478191, Verbindung

Produkt 1

HCID 469266539-(4-Chlorophenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenolAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

2-(3,4,5-Tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenone (61.6 mg, 56.1 μmol) was dissolved in dehydrated THF (3 mL), 4-chlorophenyl-magnesium bromide (200 μmol) was added, and the mixture was stirred at 40° C. for 3 hours. After evaporation of the solvent, 0.5N hydrochloric acid (6 mL) was added to the residue to allow crystallization. The crystals were collected by filtration, washed well with hydrochloric acid, water and methanol in this order to give 9-(4-chloro-phenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenol (64.1 mg, 53.0 μmol, 94%).

Aufarbeitung

  1. customAfter evaporation of the solvent, 0.5N hydrochloric acid (6 mL)
  2. additionwas added to the residue
  3. customcrystallization
  4. filtrationThe crystals were collected by filtration
  5. washwashed well with hydrochloric acid, water and methanol in this order

Quellen und Nachweise

ORD-Eintrag
ord-87ddbc1deda54ea08d89432464e62b64
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569453B2

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