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

HRID 2052043Notes

Reaction equation

HRID 2052043 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-d9f821b549924583a287850a36eb1207
Source dataset
uspto-grants-1980_01
Patent number
US04182764

Reaction notes

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