4-Hydroxybenzaldehyde → 4-(6-Hydroxyhexoxy)benzaldehyde

HRID 970250Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970250
[OH-].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[I-].[Na+].Cl[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]>O.C(O)C>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1

Komponenten

7

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 748286-Chloro-1-hexanol

Produkt 1

HCID 150510824-(6-Hydroxyhexoxy)benzaldehydeAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 40 g (1 mole) of sodium hydroxide in 60 ml of water and 400 ml of ethanol were added 122.12 g (1 mole) of 4-hydroxybenzaldehyde, 30 g of sodium iodide and 136.62 g (1 mole) of 1-chloro-6-hydroxyhexane. The mixture was heated at reflux for 24 hours under a nitrogen atmosphere. After cooling, the mixture was filtered and the solvent was removed under reduced pressure. Water (400 ml) was added to the residue and the mixture was extracted twice with 400 ml of ethyl acetate. The ethyl acetate layers were extracted twice with 200 ml of 5% aq. sodium hydroxide, and once with 200 ml of brine, dried over magnesium sulfate, and the solvent was evaporated. A brown oil (202 g, 91%) was obtained, which crystallized slowly.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 hours under a nitrogen atmosphere
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe solvent was removed under reduced pressure
  6. additionWater (400 ml) was added to the residue
  7. extractionthe mixture was extracted twice with 400 ml of ethyl acetate
  8. extractionThe ethyl acetate layers were extracted twice with 200 ml of 5% aq. sodium hydroxide
  9. dry with materialonce with 200 ml of brine, dried over magnesium sulfate
  10. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c9c9bdf946be4a7fb3eab5016f1e6009
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07311948B2

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