Sodium Cyanide → 4-Hydroxybenzyl cyanide

HRID 1834227Notes

Reaction equation

HRID 1834227 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1>CO>[C:1]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)#[N:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 356844-(Chloromethyl)-phenol2×

Product 1

HCID 265484-Hydroxybenzyl cyanideYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of p-chloromethyl phenol in acetonitrile (Example 12) was reacted with equimolar sodium cyanide in excess methanol (800 parts methanol/mole sodium cyanide) and the reaction mixture was refluxed for one hour. The oil after solvent evaporation (washed as in Experiment 18) was fractionated to yield 45% of α-cyano-p-cresol (b.p. 150°-155°/1 mm. of mercury; M.P. 68°-70°). Infrared spectra confirmed the identity of the product.

Workup

  1. temperaturethe reaction mixture was refluxed for one hour
  2. customThe oil after solvent evaporation (washed as in Experiment 18)

Sources & evidence

ORD record
ord-0062ed53f5364dbd8d634e39ac751f2b
Source dataset
uspto-grants-1978_01
Patent number
US04069340

Reaction notes

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