Thionyl Chloride → 3-methoxy-4-nitro-benzoyl Chloride
Reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:10](O)=[O:11]>O1CCOCC1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[C:10]([Cl:3])=[O:11]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Thionyl chloride 3.7 mL, (50 mmol) was added drop wise, at room temperature, to a stirred solution of 3-methoxy4-nitro-benzoic acid ( 1.0 g, 5.07 mmol) in 15 mL of dioxane under a nitrogen atmosphere. After the addition was complete, the reaction was allowed to stir at room temperature for 1 hr. The reaction flask was then fitted with a distillation head, and excess thionyl chloride and about ½ of the solvent was removed by distillation in a 120° C. oil bath. The remaining solvent was removed by rotary evaporation, and the residue was taken up in 20 mL toluene and again about ½ of the solvent was removed by distillation. The remaining solution was then cooled to 0° C., and the white solid which precipitated, was collected by suction filtration, and rinsed with 1-1 Et2O-hexane. 1H-NMR (400 MHz, CDCl3) δ 7.87 (d, J=7.83 Hz, 1H), 7.82 (d, J=7.83 Hz, 1H), 7.77 (s, 1H), 4.04 (s, 3H).
Workup
- customat room temperature
- additionAfter the addition
- customwas removed by distillation in a 120° C. oil bath
- customThe remaining solvent was removed by rotary evaporation
- customwas removed by distillation
- temperatureThe remaining solution was then cooled to 0° C.
- customthe white solid which precipitated
- filtrationwas collected by suction filtration
- washrinsed with 1-1 Et2O-hexane
Sources & evidence
- ORD record
- ord-acbe810c50354168b9db643d3ebc47d0
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07608618B2
Reaction notes
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