4-Methoxybenzaldehyde → 3-Chlorobenzoic Acid
Reaction equation
N[C@@H](C(O)=O)C(C)C.COC1C=CC(C=O)=CC=1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([O:28]O)=[O:27])[CH:21]=1>ClCCl>[Cl:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[C:26]([OH:28])=[O:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
23.4 g (0.1 mol) of the Schiff base of D-valine and anisaldehyde prepared according to Ia) was dissolved, with stirring, in 130 ml of dry dichloromethane. The solution was cooled to 5° C. or lower in an ice bath. Then 20.6 g (0.12 mol) of meta-chloroperbenzoic acid was added, with stirring, to the solution cooled to 5° C. or lower. The stirring was continued and the temperature was allowed to rise to room temperature, after which the stirring was continued for 4 more hours. After about 0.5 hour's stirring at room temperature the mixture became turbid as a result of the crystallization of meta-chlorobenzoic acid. After the reaction, in which all the meta-chlorobenzoic acid formed crystallized, the reaction mixture was filtered and the filtered solution was evaporated until dry.
Workup
- dissolutionwas dissolved
- temperaturecooled to 5° C.
- customto rise to room temperature
- stirringAfter about 0.5 hour's stirring at room temperature the mixture
Sources & evidence
- ORD record
- ord-179be85cceb04dc2a087288796100d4d
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05072041
Reaction notes
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