Methanol → Methyl 4-Chloro-2-methylbenzoate

Reaktionsgleichung

[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

Edukt 4

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 14798Sodium Hydroxide

HCID 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.