Potassium Iodide → HCID 12395633, compound

HRID 867515Notes

Reaction equation

HRID 867515 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[OH:19].Cl[CH2:21][C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH:14]1([C:7]2([CH3:13])[CH2:6][C:5]3[C:9](=[C:10]([Cl:11])[C:2]([Cl:1])=[C:3]([O:19][CH2:21][C:22]#[N:23])[CH:4]=3)[C:8]2=[O:12])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 123955886,7-Dichloro-2-cyclopentyl-5-hydroxy-2-methylindan-1-one

Product 1

HCID 12395633HCID 12395633, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6,7-dichloro-2-cyclopentyl-5-hydroxy-2-methyl-2,3-dihydro-1H-inden-1-one (9.0 g, 30 mmole), chloroacetonitrile (2.5 g, 33 mmole), potassium carbonate (4.15 g), and potassium iodide (0.5 g) in acetone (150 ml) was stirred at reflux for 19 hours. Concentration to dryness in vacuo yielded an oil that crystallized upon trituration with water. Recrystallization from benzene-cyclohexane (ca. 1:3 by volume) gave the title compound (8.5 g), m.p. 129°-131°.

Workup

  1. temperatureat reflux for 19 hours
  2. concentrationConcentration to dryness in vacuo
  3. customyielded an oil that
  4. customcrystallized upon trituration with water
  5. customRecrystallization from benzene-cyclohexane (ca. 1:3 by volume)

Sources & evidence

ORD record
ord-2fd8de26de934d05abf8f90b88a7e8f3
Source dataset
uspto-grants-1988_10
Patent number
US04775695

Reaction notes

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