Dimethyl Sulfate → Methyl 5-chloro-2-methoxybenzoate

HRID 330289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330289
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5](O)=[CH:4][CH:3]=1.[C:12](=O)([O-])[O-].[K+].[K+].S([O:23][CH3:24])(OC)(=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:12])=[O:8]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 94475-Chlorosalicylic AcidHCID 11430Potassium Carbonate

Produkt 1

HCID 118574Methyl 5-chloro-2-methoxybenzoateAusbeute 99,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 5-chlorosalicylic acid (20.0 g, 0.116 mol), potassium carbonate (40.3 g, 0.290 mol), and dimethyl sulfate (36.5 g, 0.290 mol) in acetone (300 mL) was heated at reflux for 18 hours. The mixture was cooled, concentrated, diluted with H2O, and extracted with ethyl acetate (3×150 mL). The extracts were washed with H2O and saturated NaCl, dried (MgSO4), and concentrated to give 23.10 g (99%) of product as a brown oil.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. additiondiluted with H2O
  6. extractionextracted with ethyl acetate (3×150 mL)
  7. washThe extracts were washed with H2O and saturated NaCl
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4b72682b21734a0ab04087188b707e53
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04895860

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