Acetone → HCID 178439265, compound

HRID 637738Notes

Reaction equation

HRID 637738 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 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A 228.3 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 extracted with three 500 milliliter portions of methylene chloride. The combined methylene chloride extract was washed with 500 milliliters of 5 percent aqueous hydrochloric acid followed by washing with 1000 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 (393.8 grams) was recovered in 94.3 percent yield as a white crystalline solid. Infrared spectrophotometric analysis of a film sample of the product confirmed the product structure (disappearance of phenolic hydroxy 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. extractionAfter twenty minutes (1200 s) the water and product mixture was extracted with three 500 milliliter portions 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 1000 milliliters of deionized water
  8. dry with materialthen drying over anhydrous sodium sulfate
  9. filtrationThe dry methylene chloride solution was filtered
  10. customsolvent removed by rotary evaporation under vacuum
  11. customBisphenol A dicyanate (393.8 grams) was recovered in 94.3 percent yield as a white crystalline solid

Sources & evidence

ORD record
ord-1de2d0be682645789c49d6bee70e00e5
Source dataset
uspto-grants-1985_12
Patent number
US04558115

Reaction notes

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