Phenol → 2,2-Bis(4-hydroxyphenyl)propanoic acid

HRID 1456860Notes

Reaction equation

HRID 1456860 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([OH:13])(=[O:12])[C:9]([CH3:11])=O.OS(O)(=O)=O>O>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([C:9]([C:4]2[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=2)([CH3:11])[C:8]([OH:13])=[O:12])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 1060Pyruvic AcidHCID 1118Sulfuric Acid

Product 1

HCID 6566942,2-Bis(4-hydroxyphenyl)propanoic acidYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cooled mixture of phenol (9.4 g, 0.1 mol), pyruvic acid (4.4 g, 0.05 mol), and water was added concentrated H2SO4 (4.5 mL, 18.0 g) dropwise with stirring. After 15 minutes the ice bath was removed and the reaction was warmed to room temperature and stirred for 18 hours. The reaction mixture was diluted with ethyl ether/water (200 ml 1:1) and the layers were separated. The organic layer was extracted with saturated aqueous NaHCO3. The aqueous extract was then acidified, extracted with ethyl ether, dried over MgSO4, filtered, and concentrated in vacuo to give 2,2-bis(4-hydroxyphenyl)propionic acid (6.2 g) as a colorless sticky oil.

Workup

  1. customAfter 15 minutes the ice bath was removed
  2. stirringstirred for 18 hours
  3. additionThe reaction mixture was diluted with ethyl ether/water (200 ml 1:1)
  4. customthe layers were separated
  5. extractionThe organic layer was extracted with saturated aqueous NaHCO3
  6. extractionThe aqueous extract
  7. extractionextracted with ethyl ether
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-02b3834ec4cb456dbb7a5bd75bbfa6b6
Source dataset
uspto-grants-1998_12
Patent number
US05843968

Reaction notes

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