Hydrochloric Acid → 2-(3',5'-Di(docosyloxy)benzyl)-4-methoxybenzyl alcohol

HRID 1502533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1502533
[CH2:1]([O:23][C:24]1[CH:25]=[C:26]([CH:38]=[C:39]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][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])[CH:40]=1)[CH2:27][C:28]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=1[CH:30]=[O:31])[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][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[BH4-].[Na+].Cl>C1COCC1.CCO>[CH2:42]([O:41][C:39]1[CH:38]=[C:26]([CH:25]=[C:24]([O:23][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][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:40]=1)[CH2:27][C:28]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:29]=1[CH2:30][OH:31])[CH2:43][CH2:44][CH2:45][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]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 866548892-(3',5'-Di(docosyloxy)benzyl)-4-methoxybenzaldehyde

Produkt 1

HCID 672490352-(3',5'-Di(docosyloxy)benzyl)-4-methoxybenzyl alcoholAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21873804Tetrahydrofuran ethanolLösungsmittel

Versuchsvorschrift

2-(3′,5′-Di(docosyloxy)benzyl)-4-methoxybenzaldehyde (450 mg, 0.50 mmol) was dissolved in THF-EtOH (4 ml+0.5 ml), sodium borohydride (34 mg, 0.90 mmol) was added, and the mixture was stirred for 3.5 hr. 1N Hydrochloric acid was added dropwise to the reaction mixture to quench the reaction, and the mixture was extracted with chloroform (15 ml), washed once with 1N hydrochloric acid (10 ml), and 3 times with water (5 ml). The solvent was evaporated, and the obtained residue was precipitated with methanol (5 ml) to give 2-(3′,5′-di(docosyloxy)benzyl)-4-methoxybenzyl alcohol (424 mg, 0.47 mmol, 94%).

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with chloroform (15 ml)
  4. washwashed once with 1N hydrochloric acid (10 ml), and 3 times with water (5 ml)
  5. customThe solvent was evaporated
  6. customthe obtained residue was precipitated with methanol (5 ml)

Quellen und Nachweise

ORD-Eintrag
ord-c9c79585407349249c807c2e06fc21b1
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206230B2

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