1,2-Dichloroethane → 5-Chloro-4-oxo-2,2-diphenylpentanenitrile

HRID 1278476Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1278476
ClC(C)=[CH:3][C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:5]#[N:6].C(C1C=C(SC2C=C(C)C(O)=C(C(C)(C)C)C=2)C=C(C)C=1[OH:30])(C)(C)C.ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])=O.[Na+].[Na+].[Cl:62][CH2:63][CH2:64]Cl>>[Cl:62][CH2:63][C:64](=[O:30])[CH2:3][C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:5]#[N:6]

Komponenten

6

Edukt 5

HCID 111,2-Dichloroethane2×HCID 73064,4'-Thiobis(2-tert-butyl-6-methylphenol)HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 542025064-Chloro-2,2-diphenylpentenenitrile

Produkt 1

HCID 128736295-Chloro-4-oxo-2,2-diphenylpentanenitrile

Versuchsvorschrift

A 265 g. portion of 4-chloro-2,2-diphenylpentenenitrile and 3.84 g. of bis(3-t-butyl-4-hydroxy-5-methylphenyl) sulfide were dissolved in 1 liter of 1,2-dichloroethane and heated to the reflux temperature, about 75°-80° C. To the mixture was added dropwise a solution of 276.9 g. of 3-chloroperbenzoic acid dissolved in 2.5 liters of 1,2-dichloroethane. The resulting solution was heated for 24 hours, and was then cooled to ambient temperature. Sodium sulfite solution was added until starch-iodide paper showed a negative test for peracid. The reaction mixture was then made basic by the addition of 135 g. of sodium bicarbonate in saturated aqueous solution, and the organic layer was then separated, washed with water and dried over sodium sulfate. The solvent was then evaporated away under vacuum to obtain 294.5 g. of crude product, which was crystallized from ethanol to obtain 194.3 g. of the product named in the heading, m.p. 102°-104° C.

Aufarbeitung

  1. temperatureheated to the reflux temperature, about 75°-80° C
  2. additionTo the mixture was added dropwise a solution of 276.9 g
  3. temperatureThe resulting solution was heated for 24 hours
  4. additionThe reaction mixture was then made basic by the addition of 135 g
  5. customof sodium bicarbonate in saturated aqueous solution, and the organic layer was then separated
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was then evaporated away under vacuum
  9. customto obtain 294.5 g
  10. customof crude product, which was crystallized from ethanol
  11. customto obtain 194.3 g

Quellen und Nachweise

ORD-Eintrag
ord-aec80603badd4b14aa76f6609912bd68
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04281141

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