Acetone → HCID 178439265, compound

HRID 569188Notes

Reaction equation

HRID 569188 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 98.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A 456.60 gram portion of 4,4'-isopropylidene diphenol (2.00 moles), 444.91 grams of cyanogen bromide (4.20 moles) and 1,100 milliliters of acetone were added to a reactor and maintained under a nitrogen atmosphere with stirring. The stirred solution was cooled to -5° C., then 406.82 grams of triethylamine (4.02 moles) was added to the reactor over a 60 minute (3600 s) period and so as to maintain the reaction temperature at -5° to -3° C. After completion of the triethylamine addition, the reactor was maintained at -5° to -3° C. for an additional twenty-five minutes (1500 s) followed by addition of the reactor contents to 1.5 gallons (5.685) of deionized water. After 5 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 0.05 percent by weight aqueous hydrochloric acid followed by washing with 500 milliliters of deionized water, then drying over anhydrous sodium sulfate. The dry methylene chloride extract was filtered and solvent removed by rotary evaporation under vacuum for 60 minutes (3600 s) at 100° C. Bisphenol A dicyanate (545.8 grams) was recovered in 98.1 percent yield as a light tan colored, crystalline solid. Infrared spectrophotometric analysis of a film sample of the product confirmed the product structure (disappearance of phenolic hydroxyl absorbance, appearance of cyanate absorbance).

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. temperatureso as to maintain the reaction temperature at -5° to -3° C
  3. temperaturethe reactor was maintained at -5° to -3° C. for an additional twenty-five minutes (1500 s)
  4. extractionthe 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 0.05 percent by weight aqueous hydrochloric acid
  7. washby washing with 500 milliliters of deionized water
  8. dry with materialdrying over anhydrous sodium sulfate
  9. extractionThe dry methylene chloride extract
  10. filtrationwas filtered
  11. customsolvent removed by rotary evaporation under vacuum for 60 minutes (3600 s) at 100° C
  12. customBisphenol A dicyanate (545.8 grams) was recovered in 98.1 percent yield as a light tan colored, crystalline solid

Sources & evidence

ORD record
ord-2f386de40ecc4e81ac6c204380de491b
Source dataset
uspto-grants-1988_03
Patent number
US04731426

Reaction notes

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