Bisphenol A → 4-(4'-Hydroxyphenyl)-2,2,4-trimethylchroman

HRID 1733172Notes

Reaction equation

HRID 1733172 reaction equation
[CH3:1][C:2]([C:11]1[CH:12]=[CH:13][C:14](O)=[CH:15][CH:16]=1)([C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)[CH3:3]>C(Cl)Cl>[CH3:6][C:7]1([CH3:8])[O:10][C:12]2[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:2]([C:4]2[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=2)([CH3:1])[CH2:3]1

Participants

3

Reactant 1

HCID 6623Bisphenol A

Product 1

HCID 977884-(4'-Hydroxyphenyl)-2,2,4-trimethylchroman

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a 4-necked, round bottom flask equipped with a mechanical stirrer, water cooled condenser, dropping funnel, and heated by means of electrical tape, there was placed 500 grams of methylene chloride. To the well stirred methylene chloride solution, there was added the 500 grams of molten BPA by-products, the rate of addition of the molten by-products being used to control the reflux rate of the methylene chloride. The temperature of the solvent was 40° C. and had a dark color. After the addition of about half of the molten by-products, yellow colored crystals formed in the solution. Upon completing the addition of the molten by-products, the resultant thick, yellow mixture was cooled and filtered. The filter cake was washed with fresh methylene chloride to afford a white solid. The white, chroman-I concentrate filter cake was dried at 100° C. for 24 hours.

Workup

  1. customTo a 4-necked, round bottom flask equipped with a mechanical stirrer, water cooled condenser
  2. temperatureheated by means of electrical tape, there
  3. additionthe rate of addition of the molten by-products
  4. customwas 40° C.
  5. additionAfter the addition of about half of the molten by-products, yellow colored crystals
  6. customformed in the solution
  7. additionthe addition of the molten by-products
  8. temperaturethe resultant thick, yellow mixture was cooled
  9. filtrationfiltered
  10. washThe filter cake was washed with fresh methylene chloride
  11. customto afford a white solid
  12. concentrationThe white, chroman-I concentrate
  13. filtrationfilter cake
  14. customwas dried at 100° C. for 24 hours

Sources & evidence

ORD record
ord-28400b4f6b4f4c2abb14b9a99ea739b8
Source dataset
uspto-grants-1980_12
Patent number
US04240968

Reaction notes

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