(3-Methyl-4-(trifluoromethyl)phenyl)methanol synthesis

Yield:-

Reaction Conditions:

Stage #1:3-Methyl-4-trifluoromethylbenzoic acid methyl ester with lithium borohydride in tetrahydrofuran for 3 h;Heating / reflux;
Stage #2: with hydrogenchloride;water in tetrahydrofuran

Steps:

68.3
3-Methyl-4-trifluoromethylbenzoic acid methyl ester (0.20 g) was dissolved in THF (10 mL), and lithium borohydride (0.060 g) was added to the solution. The reaction mixture was refluxed with stirring for 3 hours and cooled to room temperature. 1N hydrochloric acid was added to the reaction mixture, followed by extraction thrice, each with ethyl acetate. The extracts were combined and washed with saturated brine, followed by drying over sodium sulfate. Insoluble matter was removed by filtration, and then the filtrate was concentrated. The residue was purified by silica gel column chromatography, whereby the title compound (0.16 g) was yielded. ¹H-NMR (CDCl₃) δ : 1.72(1H,t,J=5.9Hz), 2.48-2.50(3H,m), 4.73(2H,d,J=5.6Hz), 7.26-7.26(1H,m), 7.29(1H,s), 7.59(1H,d,J=7.8Hz).

References:

Daiichi Sankyo Company, Limited EP2017263, 2009, A1 Location in patent:Page/Page column 172