Acetic Acid → HCID 14531366, compound

HRID 2231611Notes

Reaction equation

HRID 2231611 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.C(#N)[CH:12]([CH2:14][C:15]#[N:16])O.C([O-])(=O)C.[NH4+:22].C(O)(=O)C>C(OCC)C.O.C1(C)C=CC=CC=1>[C:15]([C:14]([C:12]#[N:22])=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH3:9])#[N:16]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 74694'-HydroxyacetophenoneHCID 517165Ammonium AcetateHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 14531366HCID 14531366, compoundYield 770.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 92.0 g of p-hydroxyacetophenone, 44.6 g of malonitrile, 5.2 g of ammonium acetate, 8.1 g of acetic acid and 500 ml of toluene was boiled on a water separator for 2 hours while stirring. After cooling, the two-phase mixture was diluted with 700 ml of diethyl ether. The dark red solution was washed four times with 50 ml of saturated sodium chloride solution, dried over sodium sulphate, filtered and evaporated. By fractional crystallization from diisopropyl ether there were obtained 95.7 g of p-(2,2-dicyano-1-methylvinyl)phenol, m.p. 120.5°-121.5° C.

Workup

  1. temperatureAfter cooling
  2. washThe dark red solution was washed four times with 50 ml of saturated sodium chloride solution
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customBy fractional crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-25335d3781874f308db787ddb0f6dbe3
Source dataset
uspto-grants-1988_11
Patent number
US04783280

Reaction notes

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