Hydrochloric Acid → Methyl 5-chloro-2,4-dimethoxybenzoate

HRID 2293535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293535
N[C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].N([O-])=O.[Na+].[ClH:20]>O.CC(C)=O>[Cl:20][C:2]1[C:3]([O:14][CH3:15])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 16638096Methyl 5-amino-2,4-dimethoxybenzoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 21477059Methyl 5-chloro-2,4-dimethoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

A 0.65 g portion of methyl 5-amino-2,4-dimethoxybenzoate was dissolved in a mixture solvent of 1.5 ml of water and 10 ml of acetone, and 1.3 ml of concentrated hydrochloric acid was added thereto, followed by dropwise addition of 0.23 g of sodium nitrite dissolved in 1 ml of water under ice-cooling and subsequent stirring for a while. Next, 0.35 g of cuprous chloride was added and the mixture was warmed up to room temperature. After completion of the reaction, insoluble matter was filtered and the resulting residue was mixed with water, extracted with ethyl acetate and then washed with water and saturated brine. After drying over anhydrous sodium sulfate, the solvent was evaporated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=500:1-40:1) to give 0.56 g of methyl 5-chloro-2,4-dimethoxybenzoate.

Aufarbeitung

  1. additionwas added
  2. temperaturecooling
  3. customAfter completion of the reaction, insoluble matter
  4. filtrationwas filtered
  5. additionthe resulting residue was mixed with water
  6. extractionextracted with ethyl acetate
  7. washwashed with water and saturated brine
  8. dry with materialAfter drying over anhydrous sodium sulfate
  9. customthe solvent was evaporated under a reduced pressure
  10. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=500:1-40:1)

Quellen und Nachweise

ORD-Eintrag
ord-34f624603428400f8ccbec79ccec8f0a
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686482

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