Acetone → HCID 178439265, compound

HRID 745843Notes

Reaction equation

HRID 745843 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 88.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A 342.5 gram portion of 4,4'-isopropylidenediphenol (1.50 moles), 333.68 grams of cyanogen bromide (3.15 moles) and 1000 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 305.09 grams of triethylamine (3.015 moles) was added to the reactor over a twenty-four minute (1440 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 0° to 7° C. for an additional forty-five minutes (2700 s), followed by addition of the reactor contents to 1 gallon of chilled deionized water. After twenty minutes (1200 s) the water and product mixture was filtered and the recovered crude crystalline product was dissolved in 1000 milliliters of methylene chloride. The methylene chloride solution was washed with 500 milliliters of 5 percent aqueous hydrochloric acid followed by washing with 500 milliliters of deionized water then drying over anhydrous sodium sulfate. The dry methylene chloride solution was filtered and solvent removed by rotary evaporation under vacuum. Bisphenol A dicyanate (370.3 grams) was recovered in 88.7 percent yield as a white 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 atmosphere
  2. temperatureso as to maintain the reaction temperature at -5° to 0° C
  3. temperaturethe reactor was maintained at 0° to 7° C. for an additional forty-five minutes (2700 s)
  4. filtrationAfter twenty minutes (1200 s) the water and product mixture was filtered
  5. customthe recovered crude crystalline product
  6. dissolutionwas dissolved in 1000 milliliters of methylene chloride
  7. washThe methylene chloride solution was washed with 500 milliliters of 5 percent aqueous hydrochloric acid
  8. washby washing with 500 milliliters of deionized water
  9. dry with materialthen drying over anhydrous sodium sulfate
  10. filtrationThe dry methylene chloride solution was filtered
  11. customsolvent removed by rotary evaporation under vacuum
  12. customBisphenol A dicyanate (370.3 grams) was recovered in 88.7 percent yield as a white crystalline solid

Sources & evidence

ORD record
ord-223360942ae542a7beb4be9f6d20add8
Source dataset
uspto-grants-1986_07
Patent number
US04600760

Reaction notes

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