4-Nitrobenzoic Acid → 4-Nitrobenzoyl chloride
Reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:15])=O>CN(C=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([Cl:15])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 78 °C
Procedure
4-Nitrobenzoic acid, thionyl chloride and DMF were placed in a 3-litre 4-necked glass flask and heated for 2 hours at 78° C. under reflux. The end of the reaction was monitored by the clarity of the reaction mixture. There was a clear solution at the end of the reaction. Thionyl chloride was removed under reduced pressure. Dichloroethane (1 litre) was added, and evporation was carried out to yield 4-nitrobenzoyl chloride in the form of a solid. The solid was dissolved in dichloroethane (1 litre). Dichloroethane (10 litres) was introduced into a 20-litre glass flask and cooled to 0° C. Aluminium chloride was added at 0-5° C. The 4-nitrobenzoyl chloride prepared above, dissolved in dichloroethane, was then added dropwise at 0-5° C. Phenoxypropionic acid was added in portions to the reaction composition at 0.5° C., and stirring was carried out overnight at 25° C. The TLC was checked and the reaction composition was quenched in a mixture of hexane (8 litres) and ice-water (15 litres). The composition was stirred and the solids were filtered off. The product was washed with hexane and dried.
Workup
- temperatureunder reflux
- customat the end of the reaction
- customThionyl chloride was removed under reduced pressure
- additionDichloroethane (1 litre) was added
Sources & evidence
- ORD record
- ord-1058b08f411a4756bda2f9846a9e7747
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08034797B2
Reaction notes
Loading…