Hydrochloric Acid → (1,1'-Biphenyl)-2,3'-diol

HRID 483855

Reaction equation

HRID 483855 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCCCCCCCCCCS.Cl.C[CH:23]1[CH2:29][C:28](C)(C)[CH2:27][C:25](=[O:26])[CH2:24]1>>[CH:29]1[CH:28]=[C:27]([C:3]2[CH:4]=[CH:5][CH:6]=[C:1]([OH:7])[CH:2]=2)[C:25]([OH:26])=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 313Hydrochloric Acid3×HCID 996Phenol2×HCID 81951-DodecanethiolHCID 133983,3,5-Trimethylcyclohexanone

Product 1

HCID 33665(1,1'-Biphenyl)-2,3'-diol

Procedure

7.5 mol (705 g) phenol and 0.15 mol (30.3 g) dodecylthiol are introduced into a 1-liter round-bottomed flask equipped with a stirrer, dropping funnel, thermometer, reflux condenser and gas inlet pipe and saturated with dry HCl gas at 28° to 30° C. A solution of 1.5 mol (210 g) dihydroisophorone (3,3,5-trimethylcyclohexan-1-one) and 1.5 mol (151 g) phenol is added dropwise to the resulting solution over a period of 3 hours, HCl gas continuing to be passed through the reaction solution. After the addition, HCl gas is introduced for another 5 hours. The mixture is then left to react for 8 hours at room temperature. The excess phenol is then removed by steam distillation. The residue is hot-extracted twice with petroleum ether (60-90) and once with methylene chloride and filtered off. Yield: 370 g, Mp: 205°-207° C.

Workup

  1. customequipped with a stirrer
  2. temperaturethermometer, reflux condenser and gas inlet pipe
  3. customat 28° to 30° C
  4. additionis introduced for another 5 hours
  5. waitThe mixture is then left
  6. customto react for 8 hours at room temperature
  7. customThe excess phenol is then removed by steam distillation
  8. extractionThe residue is hot-extracted twice with petroleum ether (60-90) and once with methylene chloride
  9. filtrationfiltered off

Sources & evidence

ORD record
ord-d1b6ca327397496489c9a50fd43663c3
Source dataset
uspto-grants-1993_07
Patent number
US05227458

Linked notes

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