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

HRID 1754828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754828
[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 hr. 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-ad905a13fcd941989f3cf564ce7b3507
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169187B2

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