Acetone → Bisphenol A

HRID 35433

Reaction equation

HRID 35433 reaction equation
CC(C)=[O:3].[C:5]1([OH:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[Si](C)(C)C.[CH2:17](S)[CH2:18][CH2:19]C.Cl[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[OH:11][C:5]1[CH:10]=[CH:9][C:8]([C:18]([C:23]2[CH:28]=[CH:27][C:26]([OH:3])=[CH:25][CH:24]=2)([CH3:19])[CH3:17])=[CH:7][CH:6]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 996PhenolHCID 6397ChlorotrimethylsilaneHCID 7964ChlorobenzeneHCID 8012Butanethiol

Product 1

HCID 6623Bisphenol AYield 83%

Conditions

Temperature
55 °C

Procedure

Into a 250-millimiter 3-necked round-bottomed flask was charged a mixture of 11.6 grams (0.20 mole) of acetone, 75 grams (0.80 mole) of phenol, 22 grams (0.20 mole) of chlorotrimethyl silane, and 0.10 gram of butanethiol. The resulting mixture was stirred mechanically and heated at 55° C. under a nitrogen atmosphere for 3 hours. On completion of the reaction, the reaction mixture was cooled to room temperature and filtered. The solid product resulting was slurried up in chlorobenzene, filtered and washed twice with chlorobenzene. Purification by recrystallization from methanol and water afforded bisphenol A with a purity of 99.5 percent in a 83 percent yield.

Workup

  1. additionInto a 250-millimiter 3-necked round-bottomed flask was charged
  2. customOn completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. customThe solid product resulting
  6. filtrationfiltered
  7. washwashed twice with chlorobenzene
  8. customPurification
  9. customby recrystallization from methanol and water

Sources & evidence

ORD record
ord-f5c8b7b2cd3e4b34bbb92e3ac7d465ad
Source dataset
uspto-grants-1988_08
Patent number
US04766255

Linked notes

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