Acetic Acid → HCID 14531366, compound

HRID 1462608Notes

Reaction equation

HRID 1462608 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[C:11](#[N:15])[CH2:12][C:13]#[N:14].C([O-])(=O)C.[NH4+].C(O)(=O)C>C(OCC)C.O.C1(C)C=CC=CC=1>[C:13]([C:12]([C:11]#[N:15])=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH3:9])#[N:14]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 74694'-HydroxyacetophenoneHCID 8010MalononitrileHCID 517165Ammonium Acetate

Product 1

HCID 14531366HCID 14531366, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 92.0 g of p-hydroxyacetophenone, 44.6 g of malononitrile, 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-099901d083b04b12935df558f44ba02a
Source dataset
uspto-grants-1984_07
Patent number
US04460770

Reaction notes

Loading…