Phenol → 1-(4-Tert-octyl-phenoxy)-2-propanol

Participants

Reaction Steps

A 250 mL 2-neck flask was charged with 20.6 g (0.10 mol) of 4-tert-octylphenol obtained from Aldrich Chemical Co., a catalytic amount of dry, ground potassium carbonate (1.38 g, 0.010 mol) obtained from EM Science, Inc., a stir bar, and 95%. ethanol (70 mL) under argon. The side arm was then stoppered, and a condenser with an argon inlet was attached to the center neck. Stirring was commenced to dissolve the phenol, then cold propylene oxide (8.4 mL, 7.0 g, 0.12 mol) obtained from Aldrich Chemical Co. was added. The reaction was refluxed 3 hours, allowed to cool, and the ethanol was removed by rotary evaporation. The colorless oil was dissolved in 120 mL ethyl ether, and washed twice successively with 5% aqueous sodium hydroxide, followed by water. After drying over anhydrous MgSO4, the ether was evaporated off to give 25.3 g of crude product, which contained about 22 mol % unreacted phenol, and about 7 mol % of the 2-(4-tert-octyl-phenoxy)-1-propanol isomer. The product was purified by dissolving in 100 mL hexanes, and extracting with 4×50 mL 5% NaOH in 15:85 v/v water/methanol. The methanol layers were back-extracted with 50 mL hexanes obtained from EM Science, Inc. The hexanes layers were dried over anhydrous MgSO4, and the hexanes removed under vacuum to afford a combined yield of 13.3 g (50%) of material that contained less than 1% unreacted phenol. The structure of the compound was corroborated by proton (1H) and carbon-13 NMR spectrometry. Proton NMR revealed the material to contain about 7 mol % of the 2-(4-tert-octyl-phenoxy)-1-propanol isomer.

Provenance & Evidence