4-Toluenesulfonyl chloride → 2-(Cyanomethyl)benzoic acid

HRID 2100710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2100710
[C:1]1(=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[N:10]O.[OH-].[Na+].C1(C)C=CC(S(Cl)(=O)=[O:22])=CC=1>>[C:2]([CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=1[C:1]([OH:12])=[O:22])#[N:10]

Komponenten

4

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 63990382-Oximino-1-indanone

Produkt 1

HCID 811142-(Cyanomethyl)benzoic acidAusbeute 74 %

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Indan-1,2-dione-2-oxime (35 g, 0.22 mol) was added to a solution of 402.5 ml 8% NaOH, and the mixture was heated to 50° C. Then p-toluenesulfonyl chloride (54.25, 0.28 mol) was added in portions to the mixture, and the mixture was heated at 80° C. for 15 min. After cooled to room temperature, the precipitate was removed from the mixture. The filtrate was acidified with concentrated HCl to pH=3-4 and the precipitate was collected and dried to give colorless solid (26 g, 74% yield). LC-MS: 162 (MH+)

Aufarbeitung

  1. temperaturethe mixture was heated at 80° C. for 15 min
  2. temperatureAfter cooled to room temperature
  3. customthe precipitate was removed from the mixture
  4. customthe precipitate was collected
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9634be8903474002a420cdee978599e8
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572809B2

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