Water → 4-Ethynylbenzonitrile

HRID 1755617Notes

Reaction equation

HRID 1755617 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

23.5 g of 3-methyl-1-(4'-cyanophenyl)-1-butyn-3-ol was dissolved in 250 ml of toluene in nitrogen atmosphere, and 1.6 g of sodium hydride (60% in paraffin liquid) was added thereto. This was stirred for 4 hours at 80° to 90° C. The reaction solution was poured into 300 ml of water, extracted with chloroform, and washed three times with water. Toluene and chloroform were removed by distillation, and the residue was recrystallized from methanol to obtain 9.9 g of 4-cyanophenylacetylene.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. washwashed three times with water
  4. customToluene and chloroform were removed by distillation
  5. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-2455ac9f28ab4deb83bf061d41870f36
Source dataset
uspto-grants-1995_08
Patent number
US05437815

Reaction notes

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