Methanol → 2-Chloro-4-hydroxy-benzoic acid methyl ester

HRID 220853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220853
[Cl:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:2]=1[Cl:1]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 918212-Chloro-4-hydroxybenzoic acid

Produkt 1

HCID 134988302-Chloro-4-hydroxy-benzoic acid methyl ester

Versuchsvorschrift

A solution of 2-chloro-4-hydroxy-benzoic acid (3.70 g, 21.4 mmol)) in methanol (50 ml) was treated with thionyl chloride (2.4 ml, 32 mmol) dropwise and stirred for 24 hours and the solvents were removed in vacuo. The residue was dissolved in ethyl acetate and washed with sat. sodium hydrogen carbonate, dried and solvents were removed in vacuo. The residue was purified by column chromatography on silica gel (eluant with 30% EtOAc:70% cyclohexane) to yield the desired product as a yellow solid, 3.68 g, 92%.

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with sat. sodium hydrogen carbonate
  4. customdried
  5. customsolvents were removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluant with 30% EtOAc:70% cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-37cbfa3c83e44f999761ca8d6b48b97e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202858B2

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