Acetic Acid → 2-(2-Hydroxyphenyl)acetonitrile

HRID 1576896Notes

Reaction equation

HRID 1576896 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]O.C(O)(=O)C.[C-:14]#[N:15].[K+]>CS(C)=O>[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][C:14]#[N:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5146Salicyl AlcoholHCID 9032Potassium Cyanide

Product 1

HCID 105828242-(2-Hydroxyphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

29.8g of 2-hydroxybenzyl alcohol are dissolved in 250 ml of dimethylsulfoxide, together with 18g of potassium cyanide, and the mixture is heated to 125°C. 16g of glacial acetic acid are then added dropwise over the course of 1 hour and the mixture is stirred for a further 2 hours at 125°C. The dimethylsulfoxide is removed in vacuo and the residue is stirred with 200 ml of water and 150 ml of chloroform. The chloroform phase is separated off and the aqueous phase is re-extracted with 150 ml of chloroform. The combined chloroform phases are extracted by shaking with water and dried with sodium sulfate. After distilling off the chloroform, an oil remains, which solidifies on cooling. Yield: 19.8g = 60.5% of theory. Recrystallization from benzene/ligroin: melting point 118°C.

Workup

  1. customThe dimethylsulfoxide is removed in vacuo
  2. stirringthe residue is stirred with 200 ml of water and 150 ml of chloroform
  3. customThe chloroform phase is separated off
  4. extractionthe aqueous phase is re-extracted with 150 ml of chloroform
  5. extractionThe combined chloroform phases are extracted
  6. stirringby shaking with water
  7. dry with materialdried with sodium sulfate
  8. distillationAfter distilling off the chloroform
  9. temperatureon cooling
  10. customRecrystallization from benzene/ligroin

Sources & evidence

ORD record
ord-b2acf263902d4f469be9ff6a0ebd0879
Source dataset
uspto-grants-1976_09
Patent number
US03983160

Reaction notes

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