Dichloromethane → 3-Chlorobenzoic Acid

HRID 2372911Notes

Reaction equation

HRID 2372911 reaction equation
N[C@@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])C.CO[C:11]1C=CC(C=O)=[CH:15][CH:16]=1.[Cl:19]CCl>>[Cl:19][C:16]1[CH:15]=[C:2]([CH:3]=[CH:5][CH:11]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 312444-MethoxybenzaldehydeHCID 71563D-Valine

Product 1

HCID 4473-Chlorobenzoic Acid

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. 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 evaporation until dry.

Workup

  1. dissolutionwas dissolved
  2. customto rise to room temperature

Sources & evidence

ORD record
ord-7a172da08249415e978b824ed5381147
Source dataset
uspto-grants-1992_03
Patent number
US05101036

Reaction notes

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