4-Hydroxybenzyl Alcohol → 4-Hydroxybenzyl cyanide

HRID 355171Notes

Reaction equation

HRID 355171 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]O)=[CH:4][CH:3]=1.[C-:10]#[N:11].[Na+].C(OCC)=O>C(O)C>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][C:10]#[N:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1254-Hydroxybenzyl AlcoholHCID 8025Ethyl formateHCID 8929Sodium Cyanide

Product 1

HCID 265484-Hydroxybenzyl cyanideYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.96 g. para-hydroxybenzyl alcohol 2.4 g. sodium cyanide 12 ml. ethanol and 12 ml. ethyl formate is heated with stirring under reflux for a period of ninety minutes. The reaction product is then subjected to the same isolation process as in Example 1 to give a 94% yield of crude product showing a melting point of 58°-61° C. uncorrected.

Workup

  1. additionA mixture of 4.96 g
  2. temperatureunder reflux for a period of ninety minutes

Sources & evidence

ORD record
ord-5b26fe9aa1ff4ab9b2b5955441ade8de
Source dataset
uspto-grants-1983_03
Patent number
US04378319

Reaction notes

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