Hydrogen Peroxide → 2-(Methoxymethoxy)-5-(trifluoromethyl)-phenol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-methoxymethoxy-4-trifluoromethyl-benzene (4.6 g, 22.31 mmol) in 60 mL dry THF cooled to −78° C., BuLi (21 mL of a 1.6 m sol. in hexane, 1.5 eq.) was added drop-wise via a syringe and the mixture was stirred at low temperature for 2 h, then the cooling bath was removed and the mixture was allowed to gradually warm to 0° C. during 30 min. After cooling again to −78° C., B(OCH3)3 (3.95 g, 38 mmol, 1.7 eq.) was added to the reaction and the stirring was continued for another 1.5 h at −78° C., then the solution was allowed to warm to −10° C. during 20 min. Re-cooling to −78° C. was followed by addition of H2O2 (5.82 mL of a 30% solution in H2O, 2 eq.) and NaOHaq (5.8 mL of a 5 m aqueous solution, 1.3 eq.). This solution was stirred 16 h at r.t., then saturated NH4Cl-solution was added and the mixture was extracted twice with 30 mL EtOAc. The pooled organic fractions were washed with saturated NaCl solution, dried over MgSO4 and evaporated in vacuo. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc 4:1) to yield the desired product as a yellowish oil.

Provenance & Evidence