Sulfuric Acid → HCID 14419658, compound

HRID 329756Notes

Reaction equation

HRID 329756 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:14](=[O:18])(=O)(O)[OH:15]>C1(S(O)(=O)=O)C=CC=CC=1.ClC1C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[C:11]([S:14]([C:11]3[CH:10]=[CH:9][C:8]([OH:13])=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:12]=3)(=[O:18])=[O:15])[CH:10]=[CH:9][C:8]=2[OH:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 7017(1,1'-Biphenyl)-2-ol

Product 1

HCID 14419658HCID 14419658, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 7371Benzenesulfonic AcidCatalystHCID 7964ChlorobenzeneSolvent

Procedure

To a mixture of 391 g (2.3 mol) of o-phenylphenol, 100 g (1 mol) of 98% by weight sulfuric acid, and 100 g of chlorobenzene was added 9.5 g (0.05 mol) of benzenesulfonic acid and heated with stirring. While the generated water was distilled away with chlorobenzene and the organic phase of the distillate was refluxed into the reaction vessel, the reaction was carried out for 10 hours. At the time when the distilled water amounted to 36 milliliters and the temperature in the reaction vessel rose to 165° C., the reaction mixture was cooled by adding 500 milliliters of xylene to precipitate crystals. The crystals were recrystallized from acetone-cyclohexane mixture solution to obtain 340 g of a product (yield: 85%). The melting point of the product was between 251° to 252° C. and the results of 1H-NMR (acetone d6) were as follows.

Workup

  1. temperatureheated
  2. distillationWhile the generated water was distilled away with chlorobenzene
  3. temperaturethe organic phase of the distillate was refluxed into the reaction vessel
  4. customrose to 165° C.
  5. temperaturethe reaction mixture was cooled
  6. additionby adding 500 milliliters of xylene
  7. customto precipitate crystals
  8. customThe crystals were recrystallized from acetone-cyclohexane mixture solution

Sources & evidence

ORD record
ord-455a9083e603449ab1519696001c3de3
Source dataset
uspto-grants-1990_01
Patent number
US04892924

Reaction notes

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