Potassium Iodide → HCID 18947330, compound

HRID 1769165Notes

Reaction equation

HRID 1769165 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:8]=[CH:7][C:6]=1[OH:20])([O:3][CH3:4])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][CH2:30][C:31]#[N:32].[I-].[K+]>C(#N)C>[C:1]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:8]=[CH:7][C:6]=1[O:20][CH2:28][CH2:29][CH2:30][C:31]#[N:32])([O:3][CH3:4])=[O:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 18947334HCID 18947334, compound

Product 1

HCID 18947330HCID 18947330, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Carbomethoxy-4-(m-chlorophenylmethyloxy)-phenol, 1 gram (3.32 mmoles), was treated with 1 gram potassium carbonate, 0.4 ml 4-bromobutyronitrile, and 70 mg potassium iodide in 18 ml acetonitrile under reflux for 64 hours. Then the mixture was filtered and the filtrate was stripped in vacuo. The residue was chromatographed on silica gel using 1.3 ethyl acetate/hexanes to give 0.97 grams of the title product at 79% yield. Mp 97°-98° C. Elemental analysis. Calculated for C19H18ClNO4 : C 63.42, H 5.04, N 3.89, Cl 9.85; found: C 63.38, H 5.01, N 3.81, Cl 9.77.

Workup

  1. temperatureunder reflux for 64 hours
  2. filtrationThen the mixture was filtered
  3. customThe residue was chromatographed on silica gel using 1.3 ethyl acetate/hexanes

Sources & evidence

ORD record
ord-151b5fecaa5246a2935c3a51975467e3
Source dataset
uspto-grants-1995_01
Patent number
US05380755

Reaction notes

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