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

HRID 1956823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1956823
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

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 10.5 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4a5203039102494899cfa9a6f917fffe
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05780666

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