Benzyl Chloride → 4-(Benzyloxy)-3,5-dimethylbenzaldehyde

HRID 374295

Reaktionsgleichung

Reaktionsgleichung von HRID 374295
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:11].[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([CH3:11])[C:2]=1[O:1][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:6]=[O:7]

Komponenten

5

Edukt 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 752223,5-Dimethyl-4-hydroxybenzaldehyde

Produkt 1

HCID 5635574-(Benzyloxy)-3,5-dimethylbenzaldehydeAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4.6 g (30.6 mmol) of 4-hydroxy 3,5-dimethyl benzaldehyde (Example E), 4.4 g (35 mmol) of benzyl chloride and 4.8 g (35 mmol) of anhydrous potassium carbonate in 100 mL of acetonitrile, is stirred at reflux for 18 hours overnight. The reaction flask and the inorganic salts are washed with fresh acetonitrile and the solvent is removed on a rotary evaporator. A diethyl ether solution of the residue is washed with 2×25 mL of 1N potassium hydroxide solution, brine, dried (magnesium sulfate) and evaporated. Distillation through a short path apparatus affords 6.5 g of the title compound; bp 149°-152° C./0.50 mm (190°-195° C).

Aufarbeitung

  1. temperatureat reflux for 18 hours overnight
  2. washThe reaction flask and the inorganic salts are washed with fresh acetonitrile
  3. customthe solvent is removed on a rotary evaporator
  4. washA diethyl ether solution of the residue is washed with 2×25 mL of 1N potassium hydroxide solution, brine
  5. dry with materialdried (magnesium sulfate)
  6. customevaporated
  7. distillationDistillation through a short path apparatus

Quellen und Nachweise

ORD-Eintrag
ord-e8261633d9204225bdfc53c3c680d4ed
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166398

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