Sulfuric Acid → 3~3~,3~4~,3~5~,3~6~-Tetrahydro-3~2~H-[1~1~,2~1~:2~3~,3~1~:3~1~,4~1~:4~3~,5~1~-quinquephenyl]-2~6~,4~4~-diol

HRID 1886567Notes

Reaction equation

HRID 1886567 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.[C:14]1(=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.S(=O)(=O)(O)O>ClC1C=CC=CC=1>[C:1]1([C:7]2[CH:12]=[C:11]([C:12]3([C:17]4[CH:18]=[CH:19][C:14]([OH:20])=[C:15]([C:6]5[CH:1]=[CH:2][CH:3]=[CH:4][CH:5]=5)[CH:16]=4)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]3)[CH:10]=[CH:9][C:8]=2[OH:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7017(1,1'-Biphenyl)-2-olHCID 7967Cyclohexanone

Product 1

HCID 146178583~3~,3~4~,3~5~,3~6~-Tetrahydro-3~2~H-[1~1~,2~1~:2~3~,3~1~:3~1~,4~1~:4~3~,5~1~-quinquephenyl]-2~6~,4~4~-diol

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
60 °C

Procedure

510 g (3 mol) of o-phenylphenol and 98 g (1 mol) of cyclohexanon were mixed and the temperature was raised to 60° C. to dissolve the mixture. To the mixture was then added 150 g of 90% by weight sulfuric acid and reacted with stirring for 24 hours at 70° C. After the resulting reaction product was diluted with 1 liter of monochlorobenzene and washed three times with warm water, the organic phase was heated to 190° C. under reduced pressure to remove the solvent and the unreacted materials. After dissolving the residue in 400 milliliters of methylene chloride, 500 milliliters of a 5N aqueous sodium hydroxide solution was added and stirred. After crystals were precipitated by cooling with ice, the crystals were washed twice with 500 milliliters of methylene chloride and then washed with 300 milliliters of a 2N aqueous sodium hydroxide solution. After adding 2 liters of 2N hydrochloric acid and stirring, the crystals were filtered, washed five times with water, and then recrystallized from acetone-cyclohexane mixture solution.

Workup

  1. dissolutionto dissolve the mixture
  2. customreacted
  3. customAfter the resulting reaction product
  4. washwashed three times with warm water
  5. temperaturethe organic phase was heated to 190° C. under reduced pressure
  6. customto remove the solvent
  7. dissolutionAfter dissolving the residue in 400 milliliters of methylene chloride
  8. addition500 milliliters of a 5N aqueous sodium hydroxide solution was added
  9. stirringstirred
  10. customAfter crystals were precipitated
  11. temperatureby cooling with ice
  12. washthe crystals were washed twice with 500 milliliters of methylene chloride
  13. washwashed with 300 milliliters of a 2N aqueous sodium hydroxide solution
  14. additionAfter adding 2 liters of 2N hydrochloric acid
  15. stirringstirring
  16. filtrationthe crystals were filtered
  17. washwashed five times with water
  18. customrecrystallized from acetone-cyclohexane mixture solution

Sources & evidence

ORD record
ord-3c26ecdc31494a65b6fb9b1922bbfe62
Source dataset
uspto-grants-1992_09
Patent number
US05151531

Reaction notes

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