Phenol → 4-[2-(4-hydroxyphenyl)-2-adamantyl]phenol

HRID 1406603Notes

Reaction equation

HRID 1406603 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=O)[CH2:8]2.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:19](S)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[OH:26]S(O)(=O)=O>O>[OH:18][C:12]1[CH:17]=[CH:16][C:15]([C:2]2([C:21]3[CH:22]=[CH:23][C:24]([OH:26])=[CH:19][CH:20]=3)[CH:3]3[CH2:9][CH:7]4[CH2:6][CH:5]([CH2:10][CH:1]2[CH2:8]4)[CH2:4]3)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 996PhenolHCID 1118Sulfuric AcidHCID 81061-HexanethiolHCID 64151Adamantanone

Product 1

HCID 4332744-[2-(4-hydroxyphenyl)-2-adamantyl]phenolYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2,2-Bis(4-hydroxyphenyl)adamantane (2,2-BPA) was synthesized as an aromatic diol monomer. 2-Adamantanone (4.0 g, 26.6 mmol), phenol (18.74 mL, 213 mmol) and 1-hexanethiol (0.24 mL, 1.69 mmol) were added to a 50-mL 2-bulb flask and stirred at 80° C. After the reactants were completely dissolved, H2SO4 (1.49 mL, 26.6 mmol) was added and reaction was performed under nitrogen flow for 24 hours. After the reaction was completed, the reaction solution was cooled to 50° C. and, after adding to 20 mL of water, extracted 3 times with 40 mL of chloroform. The organic layer was washed 3 times with 40 mL of water and water was removed from the organic layer by adding MgSO4, stirring and filtering. After removing the solvent by distillation under reduced pressure, followed by recrystallization with ethanol, pure 2,2-bis(4-hydroxyphenyl)adamantane (2,2-BPA, yield: 43%) was obtained. Melting temperature was 318° C.

Workup

  1. dissolutionAfter the reactants were completely dissolved
  2. customreaction
  3. customfor 24 hours
  4. temperaturethe reaction solution was cooled to 50° C.
  5. extractionextracted 3 times with 40 mL of chloroform
  6. washThe organic layer was washed 3 times with 40 mL of water and water
  7. customwas removed from the organic layer
  8. additionby adding MgSO4
  9. stirringstirring
  10. filtrationfiltering
  11. customAfter removing the solvent
  12. distillationby distillation under reduced pressure
  13. customfollowed by recrystallization with ethanol

Sources & evidence

ORD record
ord-718642a4c515409a90ac507a402b5b10
Source dataset
uspto-grants-2014_12
Patent number
US08916672B2

Reaction notes

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