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Water → 3,4-Bis(dodecyloxy)benzaldehyde

HRID 1176969
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1176969
[C:1]([O-:4])([O-])=O.[K+].[K+].Br[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1O)[CH:24]=[O:25].O>CN(C=O)C>[CH2:8]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][C:28]=1[O:4][CH2:1][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH3:8])[CH:24]=[O:25])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 87683,4-DihydroxybenzaldehydeHCID 89191-BromododecaneHCID 11430Potassium Carbonate

Produkt 1

HCID 27249313,4-Bis(dodecyloxy)benzaldehydeAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

K2CO3 (50.03 g, 0.362 mol) and 1-bromododecane (90.3 g, 0.362 mol) were added to a solution of 3,4-dihydroxybenzaldehyde (25.0 g, 0.181 mol) in 500 mL of DMF. The reaction mixture was heated at 100° C. for 2 days. The mixture was poured into H2O and extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The crude product was recrystallized from MeOH to give an off-white solid (64.8 g, 72.8%). mp 69-70° C. 1H NMR (200 MHz, CDCl3, δ): 9.80 (s, 1H), 7.36-7.41 (m, 2H), 6.92 (d, J=8.6 Hz, 1H), 4.03 (q, J=6.2 Hz, 4H), 1.81 (m, 4H), 1.44 (m, 4H), 1.24 (s, 32H), 0.85 (t, J=6.4 Hz, 6H). 13C{1H} NMR (200 MHz, CDCl3, δ): 190.92, 154.65, 149.42, 129.85, 126.54, 111.72, 110.93, 69.08, 31.89, 29.58, 29.34, 29.04, 28.96, 25.92, 22.66, 14.07. IR (cm−1): 2916, 2847, 1686, 1672, 1584, 1506, 1277, 1236, 1133, 807, 800. HRMS-FAB (m/z): [M+H]+ calcd for C31H55O3, 475.4151; found, 475.4156. Anal. Calcd for C31H54O3: C, 78.43; H, 11.46. Found: C, 78.46; H, 11.72.

Aufarbeitung

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. customThe solvent was removed under reduced pressure
  4. customThe crude product was recrystallized from MeOH

Quellen und Nachweise

ORD-Eintrag
ord-e7eadd41ca0d46ef8b9c1b58110e2a86
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842830B2

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