4-Hydroxybiphenyl → HCID 6496944, compound

HRID 518946Notes

Reaction equation

HRID 518946 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].O1[CH2:20][CH2:19][NH:18]C1=O>>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([O:13][CH2:20][CH2:19][NH2:18])=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 71034-Hydroxybiphenyl2×HCID 14797Potassium HydroxideHCID 739492-Oxazolidinone2×

Product 1

HCID 6496944HCID 6496944, compoundYield 23.1%

Procedure

ExxonMobil™ Aromatic 100 solvent (300 mL) was added into a 3-neck round bottom flask containing 4-phenylphenol (50.00 g, 294 mmol) and stirred for 15 minutes at room temperature. Potassium hydroxide pellets (1.9 g, 293 mmol) were added and the mixture heated to reflux temperature for 10 minutes. 2-oxazolidinone (26.5 g, 294 mmol) was added, and the reaction mixture continued to stir at reflux temperature for 4 hours. Additional 2-oxazolidinone (8.05 g, 92.4 mmol) was added and the reaction mixture was allowed to continue stirring at reflux for an additional 4 hours. After indication of complete conversion of 4-phenylphenol by TLC, the reaction mixture was allowed to cool to room temperature. The crude reaction mixture was filtered and the filtrate was collected. The solvent was evaporated in vacuo to obtain 14.5 g (23%) of the amine as a white solid. 1H NMR (DMSO, 400 MHz) δ 7.63-7.55 (m, 4H), 7.45-7.40 (m, 2H), 7.34-7.28 (m, 1H), 7.05-7.00 (m, 2H), 3.95 (dd, 2H, J=5.8, 5.8 Hz), 2.89 (dd, 2H, J=5.8, 5.8 Hz). 13C NMR (DMSO, 400 MHz) δ 158.3, 139.8, 132.4, 128.8, 127.7, 126.6, 126.1, 1 f4.9, 70.3, 41.0. MS (ESI) for C14H15NO [M+H] calc. 213.28. found 213.96.

Workup

  1. additionwere added
  2. temperaturethe mixture heated
  3. temperatureto reflux temperature for 10 minutes
  4. stirringto stir
  5. temperatureat reflux temperature for 4 hours
  6. stirringto continue stirring
  7. temperatureat reflux for an additional 4 hours
  8. temperatureto cool to room temperature
  9. customThe crude reaction mixture
  10. filtrationwas filtered
  11. customthe filtrate was collected
  12. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-bf07ab287f294e49a20efa598889e2e1
Source dataset
uspto-grants-2015_08
Patent number
US09115237B2

Reaction notes

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