Salicylaldehyde → p-Pentadecanoxybenzaldehyde

HRID 2425807

Reaktionsgleichung

Reaktionsgleichung von HRID 2425807
[OH-:1].[K+].O[C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CN(C)C=O.O>[CH2:13]([O:1][C:10]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:11]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

6

Edukt 3

HCID 6998SalicylaldehydeHCID 123941-BromopentadecaneHCID 14797Potassium Hydroxide

Produkt 1

HCID 23127399p-Pentadecanoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

In a 100 ml four-necked flask, 2.79 g (42.3 mM) of 85 wt % potassium hydroxide was suspended in 30 ml of dimethylformamide, and 10 ml of a dimethylformamide solution containing 5.28 g (43.2 mM) of hydroxybenzaldehyde was added dropwise while maintaining the system at 20° C. or lower, and the resultant was aged at 30° C. for 1 hour. Next, 9.58 g (32.9 mM) of 1-bromopentadecane was added, and the resultant was aged at 70° C. for 21 hours. The reaction mixture was dispersed in water and extracted with toluene. The extract was washed with water and concentrated to give 11.03 g of a slightly colored viscous liquid. Recrystallization from hexane gave 8.91 g of p-pentadecanoxybenzaldehyde (purity: 98.3%).

Aufarbeitung

  1. additionwas added dropwise
  2. waitthe resultant was aged at 70° C. for 21 hours
  3. extractionextracted with toluene
  4. washThe extract was washed with water
  5. concentrationconcentrated
  6. customto give 11.03 g of a slightly colored viscous liquid
  7. customRecrystallization from hexane

Quellen und Nachweise

ORD-Eintrag
ord-95a989a6c5fa4ea988c17c3dbc1f2c9e
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07965534B2

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