4-Hydroxybenzaldehyde → 4-(12-Hydroxy-dodecyloxy)-benzaldehyde

HRID 987342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987342
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][OH:14].[OH:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C(C)=O)C>[OH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1

Komponenten

7

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 13789512-Bromo-1-dodecanol

Produkt 1

HCID 229875484-(12-Hydroxy-dodecyloxy)-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 12-bromododecan-1-ol (15 g, 57 mmol, see Example 1 above), 4-hydroxy-benzaldehyde (6.9 g, 57 mmol), potassium carbonate (excess), potassium iodide (trace) and tetra-n-butylammonium iodide (trace) was heated at reflux in methyl ethyl ketone (50 ml) for 16 hours. After cooling, the solids were filtered off and washed with acetone. The combined organic fractions were evaporated to dryness. Diethyl ether was added to the resultant oil and the solution was stored at 4° C. The title compound precipitated and was collected by filtration.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureAfter cooling
  3. filtrationthe solids were filtered off
  4. washwashed with acetone
  5. customThe combined organic fractions were evaporated to dryness
  6. additionDiethyl ether was added to the resultant oil
  7. customwas stored at 4° C
  8. customThe title compound precipitated
  9. filtrationwas collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-796bebe025cd41308d8a054d48c52d4a
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630128B1

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