Water → 4-(Benzyloxy)-3-chlorobenzaldehyde

HRID 39129

Reaktionsgleichung

Reaktionsgleichung von HRID 39129
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH:11]1[CH:16]=[CH:15][C:14]([CH2:17]Br)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+].O>CC#N>[CH2:17]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[Cl:1])[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 170223-Chloro-4-hydroxybenzaldehyde

Produkt 1

HCID 27354954-(Benzyloxy)-3-chlorobenzaldehydeAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 3-chloro-4-hydroxy-benzaldehyde (5.0 g, 32 mmol) and BnBr (6.6 g, 38 mmol) in CH3CN (100 mL) was added K2CO3 (8.8 g, 64 mmol). The mixture was heated at reflux for 2 hours. The resulting mixture was poured into water (100 mL), and extracted with EtOAc (100 mL×3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and evaporated under vacuum to give crude product, which was purified by column (petroleum ether/EtOAc 15:1) to give 4-benzyloxy-3-chloro-benzaldehyde (7.5 g, 95%). 1H NMR (CDCl3, 400 MHz) δ 9.85 (s, 1H), 7.93 (d, J=2.0 Hz, 1H), 7.73 (dd, J=2.0, 8.4 Hz, 1H), 7.47-7.34 (m, 5H), 7.08 (d, J=8.8 Hz, 1H), 4.26 (s, 2H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted with EtOAc (100 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customevaporated under vacuum
  7. customto give crude product, which
  8. customwas purified by column (petroleum ether/EtOAc 15:1)

Quellen und Nachweise

ORD-Eintrag
ord-071e013e61d0433f8c156e1178459920
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524767B2

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