Hydrochloric Acid → 4,4'-Bis(4-hydroxyphenyl thio)biphenyl

HRID 637813

Reaction equation

HRID 637813 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[SH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Br[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=2)=[CH:18][CH:17]=1.Cl>CN(C)C=O>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([S:7][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([S:7][C:8]4[CH:13]=[CH:12][C:1]([OH:4])=[CH:10][CH:9]=4)=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 71104,4'-DibromobiphenylHCID 11430Potassium CarbonateHCID 2401474-Mercaptophenol

Product 1

HCID 135748104,4'-Bis(4-hydroxyphenyl thio)biphenylYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (75.9 g, 0.55 mol) was charged to a 2 liter flask equipped with a stirrer, condenser, dropping funnel, thermometer and nitrogen purge. Dimethylformamide (200 ml) was added and the solution heated to 80°-90° C. 4-mercaptophenol (69.3 g, 0.55 mol) in 200 ml of dimethylformamide was added to the stirred reaction mixture over one hour. The reaction mixture was maintained at 100°-110° C. for two hours. Solid 4,4'-dibromobiphenyl (78 g, 0.25 mol) was then added over one hour. The reaction mixture was refluxed for 18 hours, cooled to room temperature, and poured into 10% HCl. The white to yellow solid was collected with suction and washed with water. The solid was treated with 5-10% NaOH and filtered once more with suction. The mother liquor was acidified to pH≈2 and the solid collected and recyrstallized from chlorobenzene/methanol. A 34% yield of pure HPSB was obtained having a melting point of 214°-217° C.

Workup

  1. customequipped with a stirrer, condenser
  2. customthermometer and nitrogen purge
  3. additionDimethylformamide (200 ml) was added
  4. temperaturethe solution heated to 80°-90° C
  5. temperatureThe reaction mixture was maintained at 100°-110° C. for two hours
  6. temperatureThe reaction mixture was refluxed for 18 hours
  7. customThe white to yellow solid was collected with suction
  8. washwashed with water
  9. additionThe solid was treated with 5-10% NaOH
  10. filtrationfiltered once more with suction
  11. customthe solid collected
  12. customA 34% yield of pure HPSB was obtained

Sources & evidence

ORD record
ord-a29b699a75e745c294ba920bc2f5eea0
Source dataset
uspto-grants-1985_12
Patent number
US04558162

Linked notes

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