Benzyl Bromide → 2-(Benzyloxy)-3-methoxybenzaldehyde

HRID 5894

Reaktionsgleichung

Reaktionsgleichung von HRID 5894
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:6]([O:7][CH3:8])[C:4]=1[OH:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:8][O:7][C:6]1[C:4]([O:5][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O:1]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 8991o-VanillinHCID 11430Potassium Carbonate

Produkt 1

HCID 12680872-(Benzyloxy)-3-methoxybenzaldehydeAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 196.0 g (1.30 mole) of o-vanillin (Aldrich), 200 g of benzyl bromide (Aldrich), 500 g of anhydrous potassium carbonate and 1,500 mL of absolute ethanol is heated, with stirring, at reflux for 6 hours. After cooling, the supernatant is decanted and the remainder is filtered. The combined filtrate and supernatant is concentrated at reduced pressure to remove solvent. The remaining oil is extracted into 1 L of ether. The ether solution is washed with 500 mL of water, 600 mL of 1% potassium hydroxide solution, and 500 mL of water and then dried (potassium carbonate) and concentrated to give 263.4 g (84% yield) of product; mp 41°-43° C. Reported mp, 43° C. (Chem. Abstr. 62:16110a).

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 6 hours
  3. temperatureAfter cooling
  4. customthe supernatant is decanted
  5. filtrationthe remainder is filtered
  6. concentrationThe combined filtrate and supernatant is concentrated at reduced pressure
  7. customto remove solvent
  8. extractionThe remaining oil is extracted into 1 L of ether
  9. washThe ether solution is washed with 500 mL of water, 600 mL of 1% potassium hydroxide solution, and 500 mL of water
  10. dry with materialdried (potassium carbonate)
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0b20c9191db0436d9a89e14bbc14aaef
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246943

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