Hydrochloric Acid → 3-Cyano-3-(3,4-dichlorophenyl)propionic acid

HRID 1721708Notes

Reaction equation

HRID 1721708 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl[CH2:13][C:14]([O-:16])=[O:15].[Na+].O.Cl>CS(C)=O>[C:10]([CH:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:13][C:14]([OH:16])=[O:15])#[N:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 23665759Sodium chloroacetate

Product 1

HCID 110646173-Cyano-3-(3,4-dichlorophenyl)propionic acidYield 66%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 18.6 g (0.10 mol) of 3,4-dichlorophenylacetonitrile and 12 g (1.03 mol) of dry sodium chloroacetate is reacted for 5 hours at room temperature in 150 ml of dry dimethyl sulfoxide, in the presence of 0.5 g (1.05 mol) of sodium tert-butylate. After the reaction, the reaction mixture is poured into 1 liter of iced water and acidified to pH<3 with hydrochloric acid. The cyanoacid is extracted with ethyl acetate, which is washed to pH>3, dried over magnesium sulfate and concentrated to dryness. The residue is solidified in 1,2-dichloroethane to give 16.1 g of the expected compound (III), which is characterized by proton NMR.

Workup

  1. customAfter the reaction
  2. extractionThe cyanoacid is extracted with ethyl acetate, which
  3. washis washed to pH>3
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8bc2fb407313421794c4f4278226832c
Source dataset
uspto-grants-1996_04
Patent number
US05512680

Reaction notes

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