Hydrochloric Acid → 2-Methoxy-4-(2',2',2'-tris(octadecyloxymethyl)ethoxy)benzyl alcohol

HRID 1502537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502537
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([CH2:54][O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])([CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].CO.[BH4-].[Na+].Cl>C1COCC1.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH2:12][C:13]([CH2:54][O:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH3:73])([CH2:34][O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH2:14][O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH:8]=[CH:7][C:4]=1[CH2:5][OH:6]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 866548902-Methoxy-4-(2',2',2'-tris(octadecyloxymethyl)ethoxy)benzaldehyde

Produkt 1

HCID 532588102-Methoxy-4-(2',2',2'-tris(octadecyloxymethyl)ethoxy)benzyl alcohol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-Methoxy-4-(2′,2′,2′-tris(octadecyloxymethyl)ethoxy)benzaldehyde (288 mg, 280 μmol) was dissolved in THF (3 ml), methanol (0.3 ml) and sodium borohydride (31.8 mg, 841 μmol) were added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was cooled to room temperature, 1N hydrochloric acid (5 ml) and chloroform (5 ml) were added, and the mixture was stirred. The aqueous layer was removed, and the organic layer was further washed twice with purified water (5 ml). The organic layer was evaporated under reduced pressure, and the residue was azeotropically distilled with acetonitrile and dried in vacuo to give 2-methoxy-4-(2′,2′,2′-tris(octadecyloxymethyl)ethoxy)benzyl alcohol.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred
  3. customThe aqueous layer was removed
  4. washthe organic layer was further washed twice with purified water (5 ml)
  5. customThe organic layer was evaporated under reduced pressure
  6. distillationthe residue was azeotropically distilled with acetonitrile
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e77d8b51375249ff86f9b3e7b124bda2
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206230B2

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