Water → Bisphenol E

HRID 866722

Reaction equation

HRID 866722 reaction equation
C(C1C=[C:7]([CH2:16][CH2:17][C:18]2[CH:23]=[C:22](C(C)(C)C)[C:21]([OH:28])=[C:20](C(C)(C)C)[CH:19]=2)[CH:8]=[C:9]([C:12]([CH3:15])(C)C)C=1O)(C)(C)C.[CH2:33]1C2C(=CC=CC=2)CCC1.[OH2:43]>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:33][CH:17]([C:18]1[CH:19]=[CH:20][C:21]([OH:28])=[CH:22][CH:23]=1)[C:16]1[CH:7]=[CH:8][C:9]([OH:43])=[CH:12][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8404TetralinHCID 1648474,4'-(1,2-Ethanediyl)bis(2,6-bis(1,1-dimethylethyl)phenol

Product 1

HCID 608116Bisphenol EYield 97%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidSolvent

Procedure

A solution of 5.0 grams (0.011 mole) of 1,2-bis(3,5-di-t-butyl-4-hydroxyphenyl)ethane dissolved in 30 milliliters of tetralin containing 0.2 gram (0.0012 mole) of p-toluensulfonic acid was heated to reflux for a total of 3 hours. The reaction mixture was cooled and poured into 50 milliliters of water. The precipitated solid was collected by suction filtration and recrystallized from ethanol to yield 2.3 grams (97 percent) of bisphenol E, melting point 199°-200° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for a total of 3 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe precipitated solid was collected by suction filtration
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9f1db7b4ffdc4dc9b504e7f12c195db1
Source dataset
uspto-grants-1978_07
Patent number
US04101391

Linked notes

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