2-Nitropropane → Methyl 2,4-dichloro-3-formylbenzoate

Participants

Reaction Conditions

Reaction Steps

To methanol in a volume of 100 ml, was added 28% methanol solution of sodium methylate in an amount of 26.61 g, and to the resulting solution, was fed dropwise 2-nitro propane in an amount of 12.29 g while cooling with ice to a temperature lower than 25° C. The mixture was then added with methyl 3-bromomethyl-2,4-dichlorobenzoate in an amount of 41.16 g and stirred for 30 minutes under heating reflux. After completing reaction, the reacted-mixture was cooled and condensed under reduced pressure. A residue obtained was then dissolved in ethyl acetate in a volume of 1,000 ml, and the resulting solution was then washed with 1% aqueous solution of sodium hydroxide while cooling with ice. An organic layer resulted was washed with water and then with saturated saline solution, and was dried over anhydrous magnesium sulfate. Crystals, which were obtained after condensation of the organic layer under reduce pressure, were washed with benzene and then with n-hexane to obtain an objective compound of methyl 2,4-dichloro-3-formylbenzoate in an amount of 22.0 g in crystalline state. The melting point of this compound is in a range of from 103° to 104° C.

Provenance & Evidence