Acetic Acid → 6-Hydroxy[1,1′-biphenyl]-3-carboxylic acid

HRID 326395Notes

Reaction equation

HRID 326395 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[O:16]CC)[C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C>O>[C:1]1([C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=2[OH:16])[C:10]([OH:12])=[O:11])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 19736806HCID 19736806, compound

Product 1

HCID 115865496-Hydroxy[1,1′-biphenyl]-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-phenyl-4-ethoxybenzoic acid (26.6 g, 0.110 mole) and 550 ml of acetic acid was added to a one-liter, three-necked, round-bottom flask equipped with a 250 ml pressure equalizing dropping funnel, thermometer, cold water condenser, nitrogen inlet adapter and a polytetrafluoroethylene-coated magnetic stir bar. The flask was purged with nitrogen and the solution was brought to reflux. Approximately 125 ml of a 48 weight percent solution of HBr was added dropwise over fifteen minutes to the refluxing solution. The solution was refluxed for 30 hours. Without cooling, the solvent was rotary evaporated off leaving a slurry of a pinkish solid. The slurry was poured into one liter of deionized water and the mixture was stirred for one hour and filtered. The filter cake was dried in an 80° C. vacuum oven for three hours yielding 3-phenyl-4-hydroxybenzoic acid.

Workup

  1. customthree-necked, round-bottom flask equipped with a 250 ml pressure
  2. customThe flask was purged with nitrogen
  3. temperatureto reflux
  4. additionApproximately 125 ml of a 48 weight percent solution of HBr was added dropwise over fifteen minutes to the refluxing solution
  5. temperatureThe solution was refluxed for 30 hours
  6. temperatureWithout cooling
  7. customthe solvent was rotary evaporated off
  8. customleaving a slurry of a pinkish solid
  9. filtrationfiltered
  10. customThe filter cake was dried in an 80° C. vacuum oven for three hours

Sources & evidence

ORD record
ord-b8a7b72ce46746f1aa79954bf53f4ea6
Source dataset
uspto-grants-1993_12
Patent number
US05268443

Reaction notes

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