Acetone → HCID 178439265, compound

HRID 483189Notes

Reaction equation

HRID 483189 reaction equation
[C:1]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[N:18]#CBr.C[C:22](C)=[O:23].C([N:27](CC)CC)C>O>[O-:17][C:14]#[N:18].[O-:23][C:22]#[N:27].[OH:10][C:7]1[CH:6]=[CH:5][C:4]([C:1]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)([CH3:3])[CH3:2])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 6623Bisphenol AHCID 8471Triethylamine2×HCID 10476Cyanogen Bromide

Product 1

HCID 178439265HCID 178439265, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A 342.45 gram portion of 4,4'-isopropylidene diphenol (1.50 moles), 333.68 grams (3.15 moles) of cyanogen bromide and 1000 milliliters of acetone were added to a reactor and maintained under a nitrogen atomsphere with stirring. The stirred solution was cooled to -5° C. then 305.09 grams of triethylamine (3.015 moles) was added to the reactor over a twenty-five minute (1500 s) period and so as to maintain the reaction temperature at -5° to 0° C. After completion of the triethylamine addition, the reactor was maintained at -5° to 5° C. for an additional fifty minutes (3000 s), followed by addition of the reactor contents to 1 gallon of chilled deionized water. After five minutes (300 s) the water and product mixture was multiply extracted with three 500 milliliter volumes of methylene chloride. The combined methylene chloride extract was washed with 500 milliliters of 5 percent aqueous hydrochloric acid followed by washing with 800 milliliters of deionized water then drying with anhydrous sodium sulfate. The dry methylene chloride extract was filtered and solvent removed by rotary evaporation under vacuum. Bisphenol A dicyanate (360.74 grams) was recovered in 86.4 percent yield as a light tan crystalline solid. Infrared spectrophotometric analysis of a film sample of the product confirmed the product structure (disappearance of phenolic hydroxyl group, appearance of --C≡N group).

Workup

  1. temperaturemaintained under a nitrogen atomsphere
  2. temperatureso as to maintain the reaction temperature at -5° to 0° C
  3. temperaturethe reactor was maintained at -5° to 5° C. for an additional fifty minutes (3000 s)
  4. extractionAfter five minutes (300 s) the water and product mixture was multiply extracted with three 500 milliliter volumes of methylene chloride
  5. extractionThe combined methylene chloride extract
  6. washwas washed with 500 milliliters of 5 percent aqueous hydrochloric acid
  7. washby washing with 800 milliliters of deionized water
  8. dry with materialthen drying with anhydrous sodium sulfate
  9. extractionThe dry methylene chloride extract
  10. filtrationwas filtered
  11. customsolvent removed by rotary evaporation under vacuum
  12. customBisphenol A dicyanate (360.74 grams) was recovered in 86.4 percent yield as a light tan crystalline solid

Sources & evidence

ORD record
ord-a0bea986dbf0403fa7fc834e6bf131a0
Source dataset
uspto-grants-1986_03
Patent number
US04578439

Reaction notes

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