2-(Trifluoromethyl)benzenemethanol

Colorless to light yellow liqui

(1) To a 1000 mL three-necked round bottom flask (mechanically stirred, Thermometer) by adding water(348.0 g), then cooled to 0 ° C and then sodium borohydride (9.5 g, 0.25 mol)After stirring for 20 min, The temperature was maintained at 5 ° C with o-trifluoromethylbenzaldehyde (87.1 g, 0.5 mol)After the drop, the reaction temperature was maintained at 10 ° C for 1 h.After completion of the reaction, methyl tert-butyl ether was added to the reaction system twice.The combined organic phases were washed with saturated brine, concentrated to no fractions under reduced pressure, To give 2-trifluoromethylbenzyl alcohol as a colorless transparent liquid, the content of> 99percent, the yield of 90percentIn the three-port flask, add 2 - trifluoromethylbenzene formaldehyde 500g, anhydrous ethanol 1500 ml, four butyl ammonium bromide 50g, stirring and dissolving, and keeping the temperature at 0 °C, adding sodium borohydride in batches 150g, each time adding 30g. After adding stirring 30min, heating up to 40 °C, reaction 2h, TLC tracking, the reaction is complete. Concentrated under reduced pressure, by adding 500 ml of water, stirring 30min, adding 1500 ml ethyl ether extraction, water washing, water-free magnesium sulfate after drying, filtration, concentration, to obtain 2 - trifluoro the methyl animal pen is mellow 450g, yield 89percent.General procedure: [0179] The reaction of benzaldehyde 4a and phenylsilane 5 was investigated in the presence of various pincer nickel complexes (1.0 molpercent) and benzyl alcohol was obtained in 99percent yield when 2 was employed (Table 1, entry1). Slightly lower yields of benzyl alcohol were observed when complexes 1 and3 were tested with longer reaction time (Table 1, entries 2 and 3). No product was observed without using Ni complexes (Table 1, entry 4). These observations suggested that complexes 1-3 serve as the catalyst and 2 was the best among them. Reaction screenings with various solvents (Table 1, entries 5-7), under different temperatures and catalyst loadings (Table 1, entries 8-11) indicated that 0.2 molpercent of 2 showed satisfactory catalyst performance in toluene at 80 °C.[01 87] General procedures for hydrosilylation of aldehyde: to a flame- dried Schlenk flask was added a solution of nickel PN3P-pincer complex 2 (1.0 mg, 2 imol) in toluene (1.0 mL), an aldehyde substrate (1.0 mmol) and PhSiH3 (49 1iL, 0.4 mmol) under an argon atmosphere. The resulting mixture was stirred at 80 °C until there was no aldehyde left (monitored by withdrawing aliquots and analyzing their 'H NIVIR spectra). The reaction was then quenched by a 10percent aqueous solution of NaOH (about 1.0 mL) with vigorous stirring for more than 12 hours. The solution containing the alcohol product was extracted with diethyl ether three times, dried over anhydrous Na2SO4, and concentrated under vacuum. The desired alcohol was further purified by flash column chromatography.

Molecular Weight:176.14
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:176.04489933
Monoisotopic Mass:176.04489933
Topological Polar Surface Area:20.2
Heavy Atom Count:12
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes