Sodium Methoxide → HCID 17989405, compound

Temperature

100 °C

4′-Chloro-3-(1,1-dichloromethyl)-4-nitrobiphenyl (0.4 g, 1.26 mmol) was dissolved in methanolic sodium methoxide (15 mL; 0.5 M). The mixture was refluxed for 12 hours under argon. The solvent was evaporated and the residue diluted in 1,4-dioxane (15 ml) and water (1 ml), then a few drops of concentrated HCl were added. The reaction mixture was stirred at 100° C. for 4 hours. The solvent was then evaporated and the crude mixture purified by flash chromatography on silica gel (eluting with dichloromethane in petroleum ether) to yield the 4′-chloro-4-nitrobiphenyl-3-carbaldehyde (0.32 g, 1.26 mmol); m/z (APCI−) 260 (40%, [M−H]−), 231 (100%). This aldehyde (0.32 g, 1.26 mmol) was dissolved in acetic acid (5 mL) and sodium perborate (0.23 g, 1.5 mmol) was added. The resulting mixture was stirred at 50° C. for 16 h. The mixture was cooled, the solvent was evaporated, ethyl acetate was added and the organic layer washed with water, dried over MgSO4 and evaporated to yield the 4′-chloro-4-nitrobiphenyl-3-carboxylic acid (0.14 g, 41%); m/z [APCI−] 276 (100%, [M−H−], 247 (60%).

1. temperatureThe mixture was refluxed for 12 hours under argon
2. customThe solvent was evaporated
3. additionthe residue diluted in 1,4-dioxane (15 ml)
4. additionwater (1 ml), then a few drops of concentrated HCl were added
5. customThe solvent was then evaporated
6. customthe crude mixture purified by flash chromatography on silica gel (eluting with dichloromethane in petroleum ether)

ORD record

ord-93184b7fe57345c3b93390b51c3accb2

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07220777B2