Acetic Acid → 2-(4'-Methoxyphenyl)-4-phenyl-3-oxobutyronitrile

HRID 36739

Reaction equation

HRID 36739 reaction equation
[C-:1]#[N:2].[K+].[CH3:4][O:5][C:6]1[CH:21]=[CH:20][C:9]([C:10](=O)[CH:11]=[CH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.CC(O)=[O:24]>O.COCCO>[CH3:4][O:5][C:6]1[CH:21]=[CH:20][C:9]([CH:10]([C:11](=[O:24])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:1]#[N:2])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 92853Ccris 2231

Product 1

HCID 199376942-(4'-Methoxyphenyl)-4-phenyl-3-oxobutyronitrileYield 75.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 80192-MethoxyethanolSolvent

Procedure

Step B Add KCN (11.27 g, 0.173 mol) in water (25 mL) to a 100° C. solution of 4'-methoxychalcone (27.51 g 0.115 mol) and HOAc (7.5 mL, 0.128 mol) in 2-methoxyethanol (200 mL). The reaction is complete in <10 min. Cool the resulting solution to room temperature and pour into a mixture of ice and water (1 L). Extract the mixture with EtOAc. Combine the organic extracts, wash with water and brine, dry over Na2SO4, filter and concentrate in vacuo. Recrystallize the resulting solid from CH2Cl2 /MeOH to provide 23.07 g (75%) of 2-(4'-methoxyphenyl)-4-phenyl-3-oxobutyronitrile, mp 115°-116° C.

Workup

  1. waitThe reaction is complete in <10 min
  2. extractionExtract the mixture with EtOAc
  3. washwash with water and brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customRecrystallize the resulting solid from CH2Cl2 /MeOH

Sources & evidence

ORD record
ord-80cfb567e35140a99d228d1fb5cf0eaf
Source dataset
uspto-grants-1995_05
Patent number
US05416118

Linked notes

Loading…