Hydrochloric Acid → Methyl 2-allyloxy-3-formyl-4-methoxybenzoate

HRID 1370163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1370163
[CH2:1](Br)[CH:2]=[CH2:3].[OH-].[K+].[OH:7][C:8]1[C:17]([CH:18]=[O:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11].Cl>CS(C)=O>[CH2:1]([O:7][C:8]1[C:17]([CH:18]=[O:19])=[C:16]([O:20][CH3:21])[CH:15]=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])[CH:2]=[CH2:3]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 219335993-Formyl-2-hydroxy-4-methoxy-benzoic acid methyl ester

Produkt 1

HCID 21933587Methyl 2-allyloxy-3-formyl-4-methoxybenzoateAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

At room temperature, 23.2 g (0.192 mol) of allyl bromide were added dropwise to a mixture of 21.0 g (0.375 mol) of potassium hydroxide and 20.2 g (0.096 mol) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in 500 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 4 hours. The mixture was subsequently added to 1.5 l of 3% strength aqueous hydrochloric acid with stirring and extracted with ethyl acetate. The combined organic phases were washed with water and dried, and the solvent was removed. Chromatography over silica gel using cyclohexane/ethyl acetate=1:2 gave 7.7 g (36% of methyl 2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish oil.

Aufarbeitung

  1. stirringwith stirring
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with water
  4. customdried
  5. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-18550df5653244d5a1c3a918df1d680d
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06583089B1

Notizen zur Reaktion

Wird geladen…