Sodium Chloride → 4-Hydroxybenzyl cyanide

HRID 262428Notes

Reaction equation

HRID 262428 reaction equation
[OH-].[Na+].[C-]#[N:4].[Na+].O.[OH:7][C:8]1[CH:18]=[CH:17][C:11]([CH:12](O)[C:13]([O-])=O)=[CH:10][CH:9]=1.[Na+].[Cl-].[Na+]>CN(C)C=O.O.C(O)=O>[OH:7][C:8]1[CH:18]=[CH:17][C:11]([CH2:12][C:13]#[N:4])=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 236981332-Hydroxy-2-(4-hydroxyphenyl)acetic acid, sodium salt hydrate

Product 1

HCID 265484-Hydroxybenzyl cyanide

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

Sodium hydroxide (4.0 g.) and sodium cyanide (5.0 g.) are added to a stirred suspension of sodium p-hydroxymandelate monohydrate (19 g. of 89% w/w material, the impurity being sodium chloride) in N,N-dimethylformamide (100 ml.) and the mixture is stirred and heated at 135° C. for 4 hours and then cooled. Formic acid (7.7 ml.) and water (200 ml.) are added and the mixture is extracted twice with methyl isobutyl ketone (100 ml. and 75 ml.). The combined extracts are washed twice with water (40 ml. each time) and are 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.

Workup

  1. temperaturecooled
  2. extractionthe mixture is extracted twice with methyl isobutyl ketone (100 ml. and 75 ml.)
  3. washThe combined extracts are washed twice with water (40 ml
  4. concentrationeach time) and are then concentrated by evaporation

Sources & evidence

ORD record
ord-9797c9b95f6a418f88ecf5a57372a77f
Source dataset
uspto-grants-1979_05
Patent number
US04154757

Reaction notes

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