Ethanol → [1-(4-Chlorophenyl)-2-oxo-cyclohexyl]-acetonitrile

HRID 2076057Notes

Reaction equation

HRID 2076057 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:18][C:19]#[N:20].C(O)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:18][C:19]#[N:20])[CH2:13][CH2:12][CH2:11][CH2:10][C:9]2=[O:14])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 38395662-(4-Chlorophenyl)cyclohexan-1-one

Product 1

HCID 68911510[1-(4-Chlorophenyl)-2-oxo-cyclohexyl]-acetonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Conditions

Temperature
22.5 °C

Procedure

A solution of 2-(4-chlorophenyl)-cyclohexanone (100 g, 0.48 mol) in N,N-dimethylformamide (0.5 L) was added slowly to a mixture of sodium hydride (13.8 g, 0.78 mol) in N,N-dimethylformamide (0.2 L), the temperature being kept below 40° C. The reaction mixture was stirred at 20-25° C. for 1.5 h when a precipitate was formed. The mixture was diluted with N,N-dimethylformamide (0.2 L), and thereafter, a solution of chloroacetonitrile (43.0 g, 0.57 mol) in N,N-dimethylformamide (0.1 L) was slowly added with cooling over 0.5 h, the temperature being kept below 25° C. The mixture was stirred for 18 h, and then, ethanol (50 mL) was slowly added. The mixture was stirred for 0.5 h and then poured onto ice-water.

Workup

  1. custombeing kept below 40° C
  2. customwas formed
  3. temperaturewith cooling over 0.5 h
  4. custombeing kept below 25° C
  5. stirringThe mixture was stirred for 18 h
  6. stirringThe mixture was stirred for 0.5 h
  7. additionpoured onto ice-water

Sources & evidence

ORD record
ord-a97c68ba187e40f9ab49a413de18d882
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

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