Methanol → Methyl 4-Chloro-2-methylbenzoate

HRID 447854

Reaktionsgleichung

Reaktionsgleichung von HRID 447854
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:19]O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[C:4]([CH3:11])[CH:3]=1

Komponenten

5

Edukt 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 3482694-Chloro-2-methylbenzoic acid

Produkt 1

HCID 22349978Methyl 4-Chloro-2-methylbenzoate

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

(Step 1) To a solution of 4-chloro-2-methylbenzoic acid (5.0 g) in methanol (40 ml) was added concentrated sulfuric acid at room temperature. The mixture was stirred at 70° C. for 3 hr, neutralized with 1N sodium hydroxide, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:19→3:7) to give methyl 4-chloro-2-methylbenzoate (5.05 g) as an oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:19→3:7)

Quellen und Nachweise

ORD-Eintrag
ord-74550971c4074f288ddf333d0a5df061
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481569B2

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