Benzyl Bromide → 5-(Benzyloxy)-2-methoxybenzaldehyde

HRID 35283

Reaktionsgleichung

Reaktionsgleichung von HRID 35283
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl.O>[CH2:12]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

7

Edukt 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 3583415-Hydroxy-2-Methoxybenzaldehyde

Produkt 1

HCID 109666945-(Benzyloxy)-2-methoxybenzaldehydeAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 21218Trioctylmethylammonium chlorideKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred suspension of 5-hydroxy-2-methoxybenzaldehyde (306.6 g, prepared by the method of Ulrich et al, J.Org.Chem., 1974, 39, 2437), benzyl bromide (355.8 g) and Adogen 464 (48.5 g) in dichloromethane (600 ml) was added a solution of sodium hydroxide (123.5 g) in water (500 ml). The mixture became warm and the suspension dissolved; additional dichloromethane (300 ml) was added to prevent crystallisation of the benzylated product. After 2 hours, the organic layer was removed, washed twice with water, once with saturated sodium chloride solution, then dried with anhydrous magnesium sulphate. The solution was concentrated, then treated with petroleum spirit to give 5-benzyloxy-2-methoxybenzaldehyde (445.7 g, 91%), m.p. 99°-100°.

Aufarbeitung

  1. customprepared by the method of Ulrich et al, J.Org.Chem
  2. temperatureThe mixture became warm
  3. dissolutionthe suspension dissolved
  4. customcrystallisation of the benzylated product
  5. customthe organic layer was removed
  6. washwashed twice with water, once with saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulphate
  8. concentrationThe solution was concentrated
  9. additiontreated with petroleum spirit

Quellen und Nachweise

ORD-Eintrag
ord-09acaa2b0fe944e185cdd2596e974e13
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766121

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