Potassium Carbonate → HCID 12685614, compound

HRID 1193648Notes

Reaction equation

HRID 1193648 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Br[CH:11]([Cl:14])[CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:14][CH2:11][CH2:12][CH2:13][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 36872Propane, bromochloro-

Product 1

HCID 12685614HCID 12685614, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-cyanophenol, 125.0 g (1.05 mole), bromochloropropane, 189.0 g (1.2 mole) and potassium carbonate, 145.0 g (1.05 mole) was heated overnight at reflux in 750 ml of acetone. The reaction mixture was filtered and stripped to dryness. The resulting residue was dissolved in chloroform and extracted with 5% sodium hydroxide. Removal of chloroform gave an oil which crystallized to a white solid. A 5 g sample was recrystallized from isopropyl ether. This furnished 1.22 g (24.4%) of white solid, m.p. 40°-44° C. which contained a dimer impurity.

Workup

  1. temperaturewas heated overnight
  2. filtrationThe reaction mixture was filtered
  3. dissolutionThe resulting residue was dissolved in chloroform
  4. extractionextracted with 5% sodium hydroxide
  5. customRemoval of chloroform
  6. customgave an oil which
  7. customcrystallized to a white solid
  8. customA 5 g sample was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-ae2955254a5e498095484d7ca078fa9d
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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