Acetic Acid → HCID 19594055, compound

HRID 612351Notes

Reaction equation

HRID 612351 reaction equation
[OH-].[K+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([O-])=[O:14].C(O)(=O)C>CO.O>[OH:14][N:13]=[C:16]1[CH:21]=[CH:20][C:19](=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH3:3])=[CH:5][CH:6]=2)[C:11]#[N:12])[CH:18]=[CH:17]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7416NitrobenzeneHCID 14797Potassium HydroxideHCID 76280p-Tolylacetonitrile

Product 1

HCID 19594055HCID 19594055, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
55 °C

Procedure

40 g of KOH are dissolved in 200 ml of methanol and heated up to 55° C. To the solution are added 25 g (0.19 mol) of 4-methylphenylacetonitrile, followed by 18 ml (0.17 mol) of nitrobenzene. The reaction mixture is stirred at 55° C. for 2.5 hrs. After cooling, 400 ml of water are added with stirring. The resulting solution is acidified by addition of 110 ml of acetic acid in 100 ml of water, leading to a yellow precipitate. The mixture is then filtered, and the solid is washed with a mixture of methanol and water, and methanol. After the solid is dried in air, 29.6 g (74%) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-(4-methylphenyl)-acetonitrile are obtained in the form of a yellow powder having a melting point of 148-151° C. (dec.).

Workup

  1. temperatureAfter cooling
  2. stirringwith stirring
  3. filtrationThe mixture is then filtered
  4. washthe solid is washed with a mixture of methanol and water, and methanol
  5. dry with materialAfter the solid is dried in air, 29.6 g (74%) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-(4-methylphenyl)-acetonitrile
  6. customare obtained in the form of a yellow powder

Sources & evidence

ORD record
ord-f1ba1db8beda47e9873fdc3a5a82e4b1
Source dataset
uspto-grants-1999_12
Patent number
US06004724

Reaction notes

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