Potassium Iodide → (1-Oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetonitrile

HRID 1447686Notes

Reaction equation

HRID 1447686 reaction equation
[CH3:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C:9]2[C:4](=[C:5]([Cl:13])[C:6]([Cl:12])=[C:7]([OH:11])[CH:8]=2)[C:3]1=[O:14].Cl[CH2:22][C:23]#[N:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[O:14]=[C:3]1[C:4]2[C:9](=[CH:8][C:7]([O:11][CH2:22][C:23]#[N:24])=[C:6]([Cl:12])[C:5]=2[Cl:13])[CH2:10][C:2]1([CH3:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 936906,7-Dichloro-5-hydroxy-2-methyl-2-phenylindan-1-one

Product 1

HCID 12423629(1-Oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

2-Methyl-2-phenyl-5-hydroxy-6,7-dichloro-1-indanone (4.61 g., 0.015 mole), chloroacetonitrile (1.13 g., 0.015 mole), potassium carbonate (2.08 g., 0.015 mole), potassium iodide (0.25 g., 0.0015 mole) and acetone (75 ml.) are heated at reflux for 23 hours. The reaction mixture is cooled to 25° C. and concentrated to dryness in vacuo to give an oily residue which on trituration with water gives 5.12 g. of (1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetonitrile which melts at 163°-165° C. on crystallization from cyclohexane:benzene, 5:1.

Workup

  1. temperatureat reflux for 23 hours
  2. concentrationconcentrated to dryness in vacuo
  3. customto give an oily residue which on trituration with water
  4. customgives 5.12 g
  5. customof (1-oxo-2-methyl-2-phenyl-6,7-dichloro-5-indanyloxy)acetonitrile which melts at 163°-165° C. on crystallization from cyclohexane

Sources & evidence

ORD record
ord-dc2bc95477f14cf6ae1b4da0721abb7f
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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