gamma-Propanol → 4-(3-Hyd-roxypropyl)-2-t-butylphenol

Participants

Reaction Conditions

Reaction Steps

3-(3',5'-Di-tert-butyl-4'-hydroxyphenyl)-1-propanol (100 g, 0.38 mol) was dissolved in 500 ml of trifluoracetic acid. The solution was stirred at 40° C. for six hours, then poured into an ice-water mixture. The mixture was extracted with methylene chloride. The methylene chloride layer was washed with aqueous sodium carbonate and evaporated. A solution of sodium hydroxide (25 g) in 400 ml of methanol was added to the residue. The mixture was stirred at room temperature for 30 minutes, neutralized with 1N hydrochloric acid and extracted with methylene chloride. The methylene chloride layer was washed with aqueous sodium carbonate and water, dried with anhydrous sodium sulfate, and evaporated. The residue was vacuum distilled to give 51 g (64%) of the product.

Provenance & Evidence