4-(3,4,5-Tris-octadecyloxy-cyclohexylmethoxy)-benzaldehyde → (4-Methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methanol

HRID 1025053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1025053
[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:73]=[CH:72][C:69]([CH:70]=[O:71])=[CH:68][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].[CH3:74][O:75][C:76]1[CH:81]=[CH:80][C:79]([Mg]Br)=[CH:78][CH:77]=1>C1COCC1>[CH3:74][O:75][C:76]1[CH:81]=[CH:80][C:79]([CH:70]([C:69]2[CH:68]=[CH:67][C:66]([O:65][CH2:64][CH:22]3[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]3)=[CH:73][CH:72]=2)[OH:71])=[CH:78][CH:77]=1

Komponenten

4

Edukt 2

HCID 595103544-(3,4,5-Tris-octadecyloxy-cyclohexylmethoxy)-benzaldehydeHCID 178491912HCID 178491912, Verbindung

Produkt 1

HCID 46935394(4-Methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methanolAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

4-(3,4,5-Tris-octadecyloxy-cyclohexylmethoxy)-benzaldehyde (130 mg, 127 μmol) was dissolved in dehydrated THF (2 mL), 4-methoxy-phenyl-magnesiumbromide (350 μmol) was added, and the mixture was stirred at 40° C. for 1.5 hours. After evaporation of the solvent, 1N hydrochloric acid (5 mL) was added to the residue to allow crystallization. The crystals were filtered, and thoroughly washed with hydrochloric acid, water and methanol in this order to give (4-methoxy-phenyl)-[4-(3,4,5-tris-octadecyloxy-cyclohexylmethoxy)-phenyl]-methanol (110 mg, 97.2 μmol, 96%).

Aufarbeitung

  1. customAfter evaporation of the solvent, 1N hydrochloric acid (5 mL)
  2. additionwas added to the residue
  3. customcrystallization
  4. filtrationThe crystals were filtered
  5. washthoroughly washed with hydrochloric acid, water and methanol in this order

Quellen und Nachweise

ORD-Eintrag
ord-89601ea556714f19930c8f039607a263
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722934B2

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