Bisphenol A → HCID 178439265, compound

HRID 463790Notes

Reaction equation

HRID 463790 reaction equation
[N:1]#[C:2]Br.[N:4]#[C:5]Br.CC(C)=[O:9].[OH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)([CH3:20])[CH3:19])=[CH:14][CH:13]=1.C(N(CC)CC)C>CC(C)=O.O>[O-:9][C:2]#[N:1].[O-:11][C:5]#[N:4].[OH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([C:21]2[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=2)([CH3:20])[CH3:19])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 6623Bisphenol AHCID 8471Triethylamine2×HCID 10476Cyanogen BromideHCID 20148758Cyanogen bromide acetone

Product 1

HCID 178439265HCID 178439265, compoundYield 91.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

A quantity of 222.45 grams of cyanogen bromide (2.10 moles) was added to a reactor containing 350 milliliters of stirred acetone under a nitrogen atmosphere. The cyanogen bromide-acetone solution was colled to -15° C., then 228.30 grams of Bisphenol A (1.00 mole) dissolved in 700 milliliters of chilled acetone was added to the reactor. The stirred solution was allowed to equilibrate at -5° C., then 203.39 grams of triethylamine (2.01 moles) was added to the reactor over a 125 minute (7500 s) period and so as to maintain the reaction temperature at -5° C. After completion of the triethylamine addition, the reactor was maintained at -5° C. for 30 minutes (1800 s), followed by addition of the reaction product to 650 milliliters of chilled water with agitation. After 15 minutes (900 s), the water and product mixture was multiply extracted with methylene chloride. The combined methylene chloride extracts were sequentially washed with dilute 5 percent hydrochloric acid, water, dilute hydrochloric acid, water and then dried over anhydrous magnesium sulfate. The dry methylene chloride extract was filtered and solvent removed by rotary evaporation under vacuum. Bisphenol A dicyanate, 255.0 grams, was recovered in 91.6 percent yield as a white crystalline solid. Infrared spectrophotometric analysis confirmed the product structure.

Workup

  1. customwas colled to -15° C.
  2. additionwas added to the reactor
  3. customto equilibrate at -5° C.
  4. temperaturethe reactor was maintained at -5° C. for 30 minutes (1800 s)
  5. extractionthe water and product mixture was multiply extracted with methylene chloride
  6. washThe combined methylene chloride extracts were sequentially washed
  7. additionwith dilute 5 percent hydrochloric acid, water, dilute hydrochloric acid, water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. extractionThe dry methylene chloride extract
  10. filtrationwas filtered
  11. customsolvent removed by rotary evaporation under vacuum
  12. customBisphenol A dicyanate, 255.0 grams, was recovered in 91.6 percent yield as a white crystalline solid

Sources & evidence

ORD record
ord-e9a87bc67b154d51bc3e86250e72f8c8
Source dataset
uspto-grants-1985_10
Patent number
US04544704

Reaction notes

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