Potassium Iodide → HCID 14174458, compound

HRID 380966Notes

Reaction equation

HRID 380966 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:11](=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[I-].[K+]>CN(C)C=O.O>[CH2:17]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[C:9]#[N:10])=[CH:4][CH:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanide

Product 1

HCID 14174458HCID 14174458, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Hydroxyphenylacetonitrile (15.3 g, 114.9 mmol) was dissolved in dimethylformamide (120 ml) and to this was added potassium carbonate (23.78 g, 172.4 mmol), benzyl bromide (20.64 g, 120.6 mmol) and potassium iodide (3.81 g, 30.0 mmol). The solution was stirred at ambient temperature for 6 hours after which water was added. 4-Benzyloxyphenylacetonitrile precipitated out of solution. The suspension was filtered and the precipitate washed with water (3×). Yield 24.8 g (97%) as yellow crystals. The title product was prepared from 4-benzyloxyphenyl-acetonitrile as described in Preparation 7.

Workup

  1. additionwas added
  2. custom4-Benzyloxyphenylacetonitrile precipitated out of solution
  3. filtrationThe suspension was filtered
  4. washthe precipitate washed with water (3×)
  5. customas described in Preparation 7

Sources & evidence

ORD record
ord-bf65484cac934fb9a0a456c5806fb43f
Source dataset
uspto-grants-2001_10
Patent number
US06303816B1

Reaction notes

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