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

Temperature

25 °C

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.

1. temperatureunder heating
2. temperaturereflux
3. customreaction
4. temperaturethe reacted-mixture was cooled
5. customcondensed under reduced pressure
6. customA residue obtained
7. washthe resulting solution was then washed with 1% aqueous solution of sodium hydroxide
8. temperaturewhile cooling with ice
9. customAn organic layer resulted
10. washwas washed with water
11. dry with materialwith saturated saline solution, and was dried over anhydrous magnesium sulfate
12. customCrystals, which were obtained
13. customafter condensation of the organic layer
14. washwere washed with benzene

ORD record

ord-8a0df82e25f24def982cbd8e1fc880c8

Source dataset

uspto-grants-1998_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05807806