Methyl iodide → HCID 11025048, compound

HRID 1291732Notes

Reaction equation

HRID 1291732 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:17])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.I[CH3:19].[OH-].[K+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:17][CH3:19])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 18920656HCID 18920656, compound

Product 1

HCID 11025048HCID 11025048, compoundYield 193%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1,2-di(p-bromophenyl)-hydroxyethane (40 g, 0.056 mol), iodomethane (150 g) and powdered potassium hydroxide (30 g) was stirred at room temperature of 3 days. The reaction mixture was transferred into a 500 mL separatory funnel and water (200 mL) was added. The resulting mixture was extracted with chloroform (150 mL×2). The combined organic phases were dried through sodium sulfate and concentrated to provide an oil which was distilled under vacuum to give the title compound (40 g, 85%). This oil solidified upon standing and was recrystallized from methanol to provide fine crystals (mp: 53-54° C.), which showed the expected proton NMR spectrum.

Workup

  1. customThe reaction mixture was transferred into a 500 mL separatory funnel
  2. extractionThe resulting mixture was extracted with chloroform (150 mL×2)
  3. dry with materialThe combined organic phases were dried through sodium sulfate
  4. concentrationconcentrated
  5. customto provide an oil which
  6. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-5ace67c5fb8544f09ce03749ad9ad103
Source dataset
uspto-grants-1998_05
Patent number
US05753757

Reaction notes

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