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

Participants

Reaction Steps

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.

Provenance & Evidence