Phenol → Phenol, 4,4'-(4-hydroxycyclohexylidene)bis-

HRID 2294900Notes

Reaction equation

HRID 2294900 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O>O1CCOCC1.O>[OH:7][C:1]1[CH:6]=[CH:5][C:4]([C:4]2([C:4]3[CH:5]=[CH:6][C:1]([OH:7])=[CH:2][CH:3]=3)[CH2:5][CH2:6][CH:1]([OH:7])[CH2:2][CH2:3]2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 1118Sulfuric Acid

Product 1

HCID 10731776Phenol, 4,4'-(4-hydroxycyclohexylidene)bis-Yield 87.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of ketal intermediate (2.8 g, 17.7 mmol) and phenol (5.64 g, 60 mmol) in dioxane (10 mL) and water (10 mL) at 0° C. was treated dropwise with conc. H2SO4 (20 mL). The mixture was allowed to warm to room temperature and stirred at this temperature for the next 6 h. The reaction mixture was then poured into ice-water and extracted with ethyl acetate. The acetate layer was washed with water, brine, dried with anhydrous MgSO4 and concentrated in vacuo to provide 4,4-bis(4-hydroxyphenyl)cyclohexanol (5 g) contaminated with phenol.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe acetate layer was washed with water, brine
  3. dry with materialdried with anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-346f47e2fd4149dda9db66f0f69cfd04
Source dataset
uspto-grants-1997_11
Patent number
US05691351

Reaction notes

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