Sodium Chloride → 4-Hydroxybenzyl cyanide

HRID 262431

Reaktionsgleichung

Reaktionsgleichung von HRID 262431
[C-]#[N:2].[Na+].[OH:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9](O)[C:10]([O-])=O)=[CH:7][CH:6]=1.[Na+].[Cl-].[Na+]>>[OH:4][C:5]1[CH:15]=[CH:14][C:8]([CH2:9][C:10]#[N:2])=[CH:7][CH:6]=1

Komponenten

4

Edukt 3

HCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 23663713Sodium 4-hydroxyphenylglycolate

Produkt 1

HCID 265484-Hydroxybenzyl cyanide

Reaktionsbedingungen

Temperatur
135 °C

Versuchsvorschrift

Sodium cyanide (25.0 g.) is added to a stirred suspension of anhydrous sodium p-hydroxymandelate (96 g. of 99% w/w material, the impurity being sodium chloride; prepared from 104 g. of monohydrate by azeotropic distillation with 500 ml. of xylene in a Dean and Stark apparatus) in N,N-dimethylformamide (100 ml.), and the mixture is heated at 135° C. for 1 hour and then cooled. Water (170 ml.) and formic acid (38 ml.) are added and the mixture is extracted twice with methyl isobutyl ketone (330 ml. and 170 ml. respectively). The combined extracts are washed twice with water (240 ml. and 180 ml. respectively) and then concentrated by evaporation. There is thus obtained a solution of p-hydroxybenzyl cyanide in methyl isobutyl ketone which is suitable for conversion to p-hydroxyphenylacetamide without further purification.

Aufarbeitung

  1. customprepared from 104 g
  2. distillationof monohydrate by azeotropic distillation with 500 ml
  3. temperaturecooled
  4. additionWater (170 ml.) and formic acid (38 ml.) are added
  5. extractionthe mixture is extracted twice with methyl isobutyl ketone (330 ml
  6. washThe combined extracts are washed twice with water (240 ml
  7. concentrationrespectively) and then concentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-28aa4e4d450c4980b51e07ba96da11ab
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154757

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