Formic Acid → 4-Hydroxy-4'-octyloxybiphenyl

HRID 1762770Notes

Reaction equation

HRID 1762770 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19](C(=O)C)=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(O)=[O:26].OO>C1(C)C=CC=CC=1>[OH:26][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][CH:12]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 784Hydrogen PeroxideHCID 146697594-n-Octyloxy-4'-acetylbiphenyl

Product 1

HCID 104943294-Hydroxy-4'-octyloxybiphenylYield 52.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-n-Octyloxy-4'-acetylbiphenyl (38.5 g, 0.119 mol), formic acid (23.8 g, 5.17 mols) and toluene (200 ml) were heated to 60° C., followed by dropwise adding a 35% H2O2 aqueous solution (160.7 g, 1.04 mol) over 1.5 hour while keeping the liquid temperature at 70°~75° C., thereafter heating at 60°~70° C. for 3 hours with stirring, cooling down to room temperature, extracting with toluene (1.5 l), washing with water till the washing water became neutral, drying, removing toluene, adding ethanol (200 ml), heating under reflux, somewhat cooling, adding a 40% NaOH aqueous solution (80 ml ), again heating under reflux for 2 hours, pouring the solution in 6N hydrochloric acid (1 l), stirring, collecting the resulting solids by suction filtering, adding toluene (300 ml), withdrawing water and recrystallizing to obtain 4-hydroxy-4'-n-octyloxybiphenyl (18.5 g). Yield: 50.6%. M.P.: 153.6° C.

Workup

  1. customat 70°~75° C.
  2. temperatureheating at 60°~70° C. for 3 hours
  3. extractionextracting with toluene (1.5 l)
  4. washwashing with water till the washing water
  5. customdrying
  6. customremoving toluene
  7. additionadding ethanol (200 ml)
  8. temperatureheating
  9. temperatureunder reflux
  10. temperaturesomewhat cooling
  11. additionadding a 40% NaOH aqueous solution (80 ml )
  12. temperatureagain heating
  13. temperatureunder reflux for 2 hours
  14. additionpouring the solution in 6N hydrochloric acid (1 l)
  15. stirringstirring
  16. customcollecting the resulting solids by suction
  17. filtrationfiltering
  18. additionadding toluene (300 ml)
  19. customwithdrawing water
  20. customrecrystallizing

Sources & evidence

ORD record
ord-45d1650ad3314bcfb19a37a95b17dc66
Source dataset
uspto-grants-1989_05
Patent number
US04834907

Reaction notes

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