Potassium Iodide → HCID 14836025, compound

HRID 2166467Notes

Reaction equation

HRID 2166467 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([Cl:14])[C:12]=1[OH:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[CH2:16][CH2:17][CH2:18][C:19]1[O:23][N:22]=[C:21]([CH3:24])[CH:20]=1.[OH-].[K+].[I-].[K+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([Cl:14])[C:12]=1[O:13][CH2:16][CH2:17][CH2:18][C:19]1[O:23][N:22]=[C:21]([CH3:24])[CH:20]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 14797Potassium HydroxideHCID 284603,5-Dichloro-4-hydroxybenzoic acid ethyl esterHCID 101034235-(3-Chloropropyl)-3-methylisoxazole

Product 1

HCID 14836025HCID 14836025, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 10.05 g ethyl 3,5-dichloro-4-hydroxybenzoate and 8.0 g 5-(3-chloropropyl)-3-methylisoxazole in 550 ml dry acetonitrile was added 4.87 g potassium hydroxide and 12.9 g potassium iodide. The reaction mixture was stirred at reflux overnight and then filtered and concentrated in vacuo. The residue was partitioned between ethyl acetate and water and the organic layer concentrated to a yellow oil. The latter was crystallized from ethyl acetate-hexane (1:4) at -50° C. to give 14 g of product, 12 g of which was used directly in the following hydrolysis reaction. A sample of the ester was purified by chromatography on silica to give pure compound, m.p. 49°-50° C.

Workup

  1. temperatureat reflux overnight
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between ethyl acetate and water
  5. concentrationthe organic layer concentrated to a yellow oil
  6. customThe latter was crystallized from ethyl acetate-hexane (1:4) at -50° C.

Sources & evidence

ORD record
ord-bf4028993f794245a1500839610933c6
Source dataset
uspto-grants-1990_07
Patent number
US04945164

Reaction notes

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