Benzyl Bromide → Benzyl 2-formylbenzoate

HRID 231404

Reaktionsgleichung

Reaktionsgleichung von HRID 231404
[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([OH:3])=[O:2].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O:3][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:2]

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 8406Phthalaldehydic acidHCID 11430Potassium Carbonate

Produkt 1

HCID 246096Benzyl 2-formylbenzoateAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 2-carboxybenzaldehyde (15.00 g, 0.100 moles), benzyl bromide (20.52 g, 0.120 moles) and potassium carbonate (41.46 g, 0.300 moles) in 250 ml of acetone under nitrogen in a 500 ml round-bottom flask equipped with a magnetic stirrer was refluxed for 6 hours and then stirred at room temperature overnight. The mixture was then filtered through Celite and the filtrate concentrated in vacuo to remove the acetone. The remaining yellow oil was dissolved in ether (200 ml) and this solution washed with saturated sodium bicarbonate solution (1×50 ml), saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo to give 20.4 g of the product as a yellow oil.

Aufarbeitung

  1. customequipped with a magnetic stirrer
  2. temperaturewas refluxed for 6 hours
  3. filtrationThe mixture was then filtered through Celite
  4. concentrationthe filtrate concentrated in vacuo
  5. customto remove the acetone
  6. dissolutionThe remaining yellow oil was dissolved in ether (200 ml)
  7. washthis solution washed with saturated sodium bicarbonate solution (1×50 ml), saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a445ef4974ce4d15b7c1f5befa2f0893
Quelldatensatz
uspto-grants-1989_07
Patentnummer
US04846873

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