Potassium Hydroxide → HCID 21731193, compound

HRID 1390531Notes

Reaction equation

HRID 1390531 reaction equation
[N+:1]([CH:4]([N+:21]([O-:23])=[O:22])[CH2:5][CH2:6][Si:7]([CH3:20])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2].[OH-].[K+].Cl([F:30])(=O)(=O)=O>CO>[F:30][C:4]([N+:1]([O-:3])=[O:2])([N+:21]([O-:23])=[O:22])[CH2:5][CH2:6][Si:7]([CH3:20])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54205431HCID 54205431, compound

Product 1

HCID 21731193HCID 21731193, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3,3-Dinitropropyl)methyldiphenylsilane was dissolved in a solution of 0.217 mol of potassium hydroxide in 900 ml of methanol. The solution was placed in a 2 l flask equipped with a glass dip tube for introducing perchloryl fluoride, a thermometer, a magnetic stirrer and an ice bath. The flask was vented to the fume-hood atmosphere by means of a mineral oil bubbler, and another bubbler as well as an inverted vacuum trap (to prevent suck back) were placed between the dip tube and a perchloryl fluoride cylinder. Perchloryl fluoride was passed into the solution at 10° until it was no longer absorbed (2 hrs). Then, 1000 ml of water was added and the solution was allowed to stir 1 hr at room temperature. An additional 1500 ml of water was added and the mixture was made basic (pH 12) with potassium hydroxide. The product was extracted with four 400 ml portions of methylene chloride. The methylene chloride solution was washed with three 1000 ml portions of water, dried and stripped of solvent. The residue, 58.5 g, was chromatographed on a 750 g column of dry silica gel, using carbon tetrachloride (30 l) for elution, to give 44.5 g (79%) of (3-fluoro-3,3-dinitropropyl)methyldiphenylsilane.

Workup

  1. customThe solution was placed in a 2 l flask
  2. customequipped with a glass dip tube
  3. customwas passed into the solution at 10° until it
  4. customwas no longer absorbed (2 hrs)
  5. additionThen, 1000 ml of water was added
  6. additionAn additional 1500 ml of water was added
  7. extractionThe product was extracted with four 400 ml portions of methylene chloride
  8. washThe methylene chloride solution was washed with three 1000 ml portions of water
  9. customdried
  10. customThe residue, 58.5 g, was chromatographed on a 750 g column of dry silica gel
  11. washfor elution

Sources & evidence

ORD record
ord-ab15b1c232d141af841108a0e43063aa
Source dataset
uspto-grants-1979_02
Patent number
US04139403

Reaction notes

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