Water → 4-Ethynylbenzonitrile

HRID 1707890Notes

Reaction equation

HRID 1707890 reaction equation
CC(O)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1.[H-].[Na+].O>C1(C)C=CC=CC=1>[C:11]([C:8]1[CH:9]=[CH:10][C:5]([C:4]#[CH:3])=[CH:6][CH:7]=1)#[N:12]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 28221554-(4-Cyanophenyl)-2-methyl-3-butyne-2-ol

Product 1

HCID 45472454-EthynylbenzonitrileYield 61.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Methyl-1-(4'-cyanophenyl)-1-butyne-3-ol (23.5 g) was dissolved in toluene (250 ml) under nitrogen atmosphere, and then sodium hydride (1.6 g) was added thereto, followed by stirring at 80° to 90° C. for 4 hours. The reaction solution was poured into water (300 ml), and then extracted with chloroform, followed by washing with water 3 times. After distilling off toluene and chloroform, the resultant was recrystallized from methanol to give 4-cyanophenylacetylene (9.9 g).

Workup

  1. extractionextracted with chloroform
  2. washby washing with water 3 times
  3. distillationAfter distilling off toluene and chloroform
  4. customthe resultant was recrystallized from methanol

Sources & evidence

ORD record
ord-e7325df26ad542f7bf8d4465886d48c6
Source dataset
uspto-grants-1994_10
Patent number
US05356558

Reaction notes

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