Potassium Carbonate → 2-Benzyloxy-5-methoxy-benzaldehyde

HRID 1096678

Reaktionsgleichung

Reaktionsgleichung von HRID 1096678
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].F[C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Br)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:17]([O:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5])[C:16]1[CH:19]=[CH:20][CH:13]=[CH:14][CH:15]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 956952-Hydroxy-5-methoxybenzaldehyde

Produkt 1

HCID 8784742-Benzyloxy-5-methoxy-benzaldehydeAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-hydroxy-5-methoxybenzaldehyde (0.152 g, 1.0 mmol) in dry MeCN (50 mL) was added 4-fluorobenzyl bromide (0.145 mg, 1.0 mmol), and anhydrous K2CO3 (0.27 g, 2.0 mmol). The mixture was refluxed under stirring for 4 h, and then evaporated in vacuo. Water (100 mL) was added and the mixture was extracted with EtOAc. The separated organic layer was dried with MgSO4, and then evaporated in vacuum. Finally, the residue was eluted through a silica gel column with n-hexane/EtOAc (4:1) to give white compound I (0.21 g, 88%).

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. customevaporated in vacuo
  3. additionWater (100 mL) was added
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialThe separated organic layer was dried with MgSO4
  6. customevaporated in vacuum
  7. washFinally, the residue was eluted through a silica gel column with n-hexane/EtOAc (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-bb68b901dcb44636822a38820b58eafb
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138360B2

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