3-(Trifluoromethyl)phenol → HCID 70618386, compound

Participants

Reaction Steps

To a solution of 4.05 g of m-trifluoromethylphenol, 40 ml of methanol and 1.19 g of sodium methoxide is added 7.71 g of methyl bromo{p-[(p-chlorophenoxy)methoxy]phenyl}acetate in 10 ml of benzene. The mixture is refluxed for 21 hours and the solvent removed under reduced pressure. The residue is triturated with dichloromethane, filtered and the filtrate chromatographed on a column of silica gel (eluent methylene chloride). The main fraction is collected and the solvent removed under reduced pressure to give an oil. The above oil is combined with 4.0 g of potassium hydroxide, 75 ml of ethanol:water (9:1) and the mixture is refluxed for 4 hours. The mixture is concentrated under reduced pressure, diluted with water and acidified with concentrated HCl. The mixture is extracted with dichloromethane, the extract is dried (MgSO4) and the solvent removed under reduced pressure to give an oil. The above oil is dissolved in ether, diisopropylamine is added and the solution is diluted with hexane. Chilling and filtering gives 6.75 g of product as off-white crystals, mp 95°-100° C.

Provenance & Evidence