Acetone → HCID 178439265, compound

HRID 65098Notes

Reaction equation

HRID 65098 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 93.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A 456.60 gram (2.00 mole) portion of 4,4'-isopropylidenediphenol, 444.91 grams (4.20 moles) of cyanogen bromide 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 406.82 grams (4.02 moles) of triethylamine was added to the reactor over a thirty minute (1800 s) period and so as to maintain the reaction temperature at -5° to -2° C. After completion of the triethylamine addition, the reactor was maintained at -5° to -3° C. for an additional forty-five minutes (2700 s), followed by addition of the reactor contents of 1.5 gallons (5.69 l) of deionized water. After 5 minutes (300 s) the water and product mixture was extracted with three 500 milliliter volumes of methylene chloride. The combined methylene chloride extract was washed with 500 milliliters of one percent aqueous hydrochloric acid followed by washing with 1000 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. Bisphenol A dicyanate (521.2 grams) was recovered in 93.6 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 --O--C≡N group).

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. temperatureso as to maintain the reaction temperature at -5° to -2° C
  3. temperaturethe reactor was maintained at -5° to -3° C. for an additional forty-five minutes (2700 s)
  4. extractionAfter 5 minutes (300 s) the water and product mixture was extracted with three 500 milliliter volumes of methylene chloride
  5. extractionThe combined methylene chloride extract
  6. washwas washed with 500 milliliters of one percent aqueous hydrochloric acid
  7. washby washing with 1000 milliliters of deionized water
  8. dry with materialthen drying over anhydrous sodium sulfate
  9. extractionThe dry methylene chloride extract
  10. filtrationwas filtered
  11. customsolvent removed by rotary evaporation under vacuum
  12. customBisphenol A dicyanate (521.2 grams) was recovered in 93.6 percent yield as a white crystalline solid

Sources & evidence

ORD record
ord-7a8acfeb85614000a180987fcea982d2
Source dataset
uspto-grants-1986_09
Patent number
US04612359

Reaction notes

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