Acetic Acid → HCID 53839455, compound

HRID 596770Notes

Reaction equation

HRID 596770 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH3:9])=[CH:4][CH:3]=1.[C:11](CC(O)=O)#[N:12].[C:17]([O-])(=O)C.[NH4+].C(O)(=O)C>C(Cl)(Cl)Cl.O.C1C=CC=CC=1>[CH3:17][C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[CH:9][C:11]#[N:12]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7467P-ChloroacetophenoneHCID 9740Cyanoacetic acidHCID 517165Ammonium Acetate

Product 1

HCID 53839455HCID 53839455, compoundYield 151.9%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

p-Chloroacetophenone (31 g.), cyanoacetic acid (25 g.), ammonium acetate (5 g.), glacial acetic acid (5 ml.), and benzene (60 ml.) were refluxed together with water separation for 90 hrs., after which time approximately 9 ml. of water had been collected. Removal of benzene and distillation of the residue gave a fraction, b.p. 115°-125°/1 mm., which was dissolved in chloroform (100 ml.) and washed with saturated sodium hydrogen carbonate solution (50 ml.) and water (50 ml.), and dried over sodium sulphate. The extract was evaporated to a viscous oil under reduced pressure and the residual oil was distilled under high vacuum to give β-methyl-p-chlorocinnamonitrile 17.5 g. (49%), b.p. 106°-113°/0.5 mm., λmax. (EtOH) 271 nm (ε 19350) (Found: C, 57.8; H, 4.7; Cl, 19.7; N, 8.1. C10H8ClN requires C, 67.6; H, 4.5; Cl, 20.0; N, 7.9%).

Workup

  1. customof water had been collected
  2. customRemoval of benzene and distillation of the residue
  3. customgave a fraction, b.p. 115°-125°/1 mm
  4. washwashed with saturated sodium hydrogen carbonate solution (50 ml.) and water (50 ml.)
  5. dry with materialdried over sodium sulphate
  6. customThe extract was evaporated to a viscous oil under reduced pressure
  7. distillationthe residual oil was distilled under high vacuum

Sources & evidence

ORD record
ord-48a749da13024f1ebf2f0c6133eb517f
Source dataset
uspto-grants-1977_03
Patent number
US04012377

Reaction notes

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