Trifluoroacetic acid → 3-(Hydroxymethyl)benzonitrile

HRID 635535

Reaktionsgleichung

Reaktionsgleichung von HRID 635535
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]N)#[N:2].N([O-])=[O:12].[Na+].FC(F)(F)C(O)=O>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:12])#[N:2]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 457594Benzonitrile, 3-(aminomethyl)-HCID 23668193Sodium Nitrite

Produkt 1

HCID 27346773-(Hydroxymethyl)benzonitrileAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

m-Cyanobenzylamine (13.2 g), sodium nitrite (10.4 g), and dimethylformamide (100 ml) were mixed together, and the mixture was vigorously stirred at room temperature. Trifluoroacetic acid (22.8 g) was added dropwise to the mixture over one hour. After completion of addition, the mixture was further allowed to react at 100° C. for one hour. For the subsequent process, the procedure of Example 1 was repeated, to thereby obtain 6.9 g of m-cyanobenzyl alcohol (bp. 128-130° C./400 Pa) (yield 52%). The purity of the product was 98%.

Aufarbeitung

  1. additionAfter completion of addition
  2. customto react at 100° C. for one hour

Quellen und Nachweise

ORD-Eintrag
ord-e100a947440847a994b06bc7d978a942
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187945B1

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