4-Hydroxybenzaldehyde → Benzaldehyde, 4-(phenylmethoxy)-

HRID 75145

Reaktionsgleichung

Reaktionsgleichung von HRID 75145
O[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[C:10](=[O:13])([O-])[O-].[K+].[K+].[I-].[K+].CN([CH:21]=[O:22])C>CCOC(C)=O.O>[CH2:6]([O:22][C:21]1[CH:8]=[CH:9][C:2]([CH:10]=[O:13])=[CH:3][CH:4]=1)[C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1

Komponenten

7

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 11430Potassium Carbonate

Produkt 1

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-Ausbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred mixture of 4-hydroxybenzaldehyde (28.2 g, 231 mmol), potassium carbonate (47.9 g, 35 mmol), potassium iodide and DMF(280 mL) benzyl bromide was added slowly at 0° C. The mixture was stirred at rt overnight. The mixture was diluted with EtOAc and water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with 1N aq HCl and dried. The solution was concentrated to give 4-benzyloxybenzaldehyde (46.5 g, 95%). 1H NMR: (CDCl3, 400 MHZ) δ=5.15 (s, 2H), 7.06 (m, 2H), 7.42(m, 5H), 7.84(m, 2H), 9.89(s, 1H).

Aufarbeitung

  1. additionwas added slowly at 0° C
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with 1N aq HCl
  5. customdried
  6. concentrationThe solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-42ea015766b440f091058e5f05edbb7f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835426B2

Verknüpfte Notizen

Wird geladen…