Water → 4-Hydroxybenzyl cyanide

HRID 262429Notes

Reaction equation

HRID 262429 reaction equation
O.[OH:2][C:3]1[CH:13]=[CH:12][C:6]([CH:7](O)[C:8]([O-])=O)=[CH:5][CH:4]=1.[Na+].[Cl-].[Na+].[C-]#[N:18].[Na+].O>CN(C)C=O.C(O)=O>[OH:2][C:3]1[CH:13]=[CH:12][C:6]([CH2:7][C:8]#[N:18])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 236981332-Hydroxy-2-(4-hydroxyphenyl)acetic acid, sodium salt hydrate

Product 1

HCID 265484-Hydroxybenzyl cyanide

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A stirred suspension of sodium p-hydroxymandelate monohydrate (50 g. of 77% w/w material, the impurity being sodium chloride) and sodium cyanide (12.5 g.) in N,N-dimethylformamide (67.5 ml.) is heated at 135° C. for 2 hours and then cooled. Water (200 ml.) and formic acid (20 ml.) are added and the mixture is extracted twice with methyl isobutyl ketone (200 ml. and 100 ml.). The combined extracts are washed twice with water (50 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 (200 ml. and 100 ml.)
  3. washThe combined extracts are washed twice with water (50 ml
  4. concentrationeach time) and are then concentrated by evaporation

Sources & evidence

ORD record
ord-1413b00779fe4c989f620225bd258016
Source dataset
uspto-grants-1979_05
Patent number
US04154757

Reaction notes

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