2-Nitrobenzyl alcohol

white to light yellow crystal powde

General procedure: A mixture of the substrate (1 mmol), ionic liquid [Dsim]HSO4 (6.5 mg, ∼0.02 mmol) in methanol (2 mL) was stirred at room temperature. After completion of the reaction (monitored by TLC), solvent was evaporated, water (1 mL) was added to the mixture, and stirred vigorously. Decantation of the mixture gave almost pure product(s). The products were characterized by comparison of their IR and NMR data. The ionic liquid was dried at 65 ◦C under vacuum to remove moisture, and then reused.General procedure: A mixture of the substrate (1 mmol) and the PEG-SANMnanocomposite (8 mg) in methanol (2 mL) was stirred at roomtemperature. After completion of the reaction (monitored byTLC), the catalyst was filtered off and the solvent was evaporatedunder reduced pressure. The crude product was purifiedby column chromatography on silica gel to yield pure alcoholsand phenols.General procedure: To a mixture of trimethylsilyl ether (1.0 mmol), 80.0 mgFe3O4ZrO2/SO42−was added and the mixture was stirredat room temperature for an appropriate time (Table 3). Aftercompletion of the reaction, as indicated by thin-layer chromatography (TLC), 10.0 mL CCl4 was added to the reactionmixture, the catalyst was separated by an external magnet, and the product was obtained by evaporation of the volatileportion under reduced pressure. All compounds are known and were characterized on the basis of their spectroscopic data(IR, 1H NMR) and by comparison with those reported in theliterature.General procedure: A Typical ProcedureIn a round-bottomed flask (10 mL), equipped with a magnetic stirrer, a solution ofbanzaldehye (0.106 g, l mmol) in CH3CN (3 mL)was prepared. The complex reducing agent (0.1 g, 0.5 mmol) was then added and the mixture wasstirred at room temperature. TLC monitored theprogress of the reaction (eluent; Hexane/EtOAc: 9/1). After completion of the reaction within 1 min, asolution of 5percent HCl (5 mL) was added to the reactionmixture and stirred for 5 min. The mixture was extracted with CH2Cl2 (3 × 10 mL) and dried overthe anhydrous sodium sulfate. Evaporation of thesolvent and short column chromatography of theresulting crude material over silica gel (0.015-0.040mm) by eluent of (Hexane/EtOAc: 9/1) afforded thepure liquid benzyl alcohol (0.105 g, 98percent yield)General procedure: In a round-bottomed flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Ni2B (0.006 g, 0.05 mmol) was then added and the mixture was stirred for 5 min.NaBH4 (0.095 g, 2.5 mmol) was also added and the resultingmixture was continued to stirring for 3 min at roomtemperature. TLC monitored the progress of the reaction(eluent, n-hexane/Et2O:5/3). After completion of the reaction, aqueous solution of KOH (2 percent, 5 mL) was addedand the mixture was stirred for 10 min. The mixture wasextracted with EtOAc (3 × 8 mL) and then dried overanhydrous Na2SO4. Evaporation of the solvent affords thepure liquid aniline in 95 percent yield (0.088 g, Table 2, entry 1).General procedure: To a 25 mL Schlenk tube containing a solution of 1 in 2 mL of THF was added an aldehyde (1.0 mmol) and (EtO)3 SiH (0.20 g, 1.2 mmol). The reaction mixture was stirred at 50–55 °C until there was no aldehyde left (monitored by TLC and GC–MS). The reaction was then quenched byMeOH (2mL) and a 10percent aqueous solution of NaOH (5 mL) with vigorous stirring at 60 °C for about 24 h.The organic product was extracted with diethyl ether (10 mL × 3), dried over anhydrous MgSO4, and concentrated under vacuum. The alcohol product was further purified using flash column chromatography (elute with 5–10percent ethyl acetate in petroleum ether). The 1H NMR and 13C NMR spectra of the alcohol products are providedin Supporting information.General procedure: To a solution of the substrate (1 mmol) in ethanol as asolvent (5 mL) in a round-bottomed flask (25 mL) equippedwith a magnetic stirrer, P(BVP)BH4 (100 mg) was addedand stirred at room temperature. The progress of thereaction was monitored by TLC. On completion of thereaction, the mixture was filtered and the used reagent waswashed successively with HCl (1.0 M, 2 10 mL) andethanol (2 5 mL). The combined filtrates were evaporatedand the pure product was obtained in moderate to excellent yields. In a few cases in which the reaction wasnot complete, the crude product was purified on silica gelwith an appropriate eluent (Scheme 1).To 136 g1, 2-bis (o-nitrophenyl) ethane(0.50 mol), 324 g of benzoquinone (3.0 mol) was added to a 1000 ml four-necked reaction flask, After heating and melting, The reaction was carried out at 135-140 ° C for 6 hours, High performance liquid chromatography tracking detection; after the reaction, the pump decompression recovery of excess benzoquinone and by-product hydroquinone;To the residue was added 408 g of methanol dissolved, Then, 19 g of sodium borohydride (0.5 mol) was added and the reaction was stirred at 15 ° C for 2 hours.After the reduction reaction, the solvent methanol was recovered and 145.4 g of a product of 160-165 ° C / 15 mmHg was collected by distillation, As the target product o-nitrobenzyl alcohol, Liquid content of 94.9percent, Yield 90.2percent;Recrystallization from toluene gave 125.2 g of pale yellow crystals, Mp 70 ~ 72 , Liquid content of 99.2percentThe total yield was 81.1percent.General procedure: The carbonyl compound (1.0 mmol) and ytterbium triflate hydrate (0.1 mmol) were dissolved in iPr-OH (2 mL). The resulting mixture was stirred at reflux overnight. The solvent was removed by anhydrous NTo a stirred solution of 2-nitrobenzaldehyde (11.0 g, 72.79 mmol) in methanol (55 ml) was added sodium borohydride (3.3 g, 88.02 mmol) at 0 °C and the reaction solution was stirred for 30 min at same temperature. The mixture was quenched with saturated aqueous ammonium chloride (150 ml) and extracted with ethyl acetate (2 x 300 ml). The combined organic layers were washed with brine (200 ml) and dried over anhydrous sodium sulphate. The organic layer was filtered and concentrated under reduced pressure. The residue obtained was purified by flash silica gel column chromatography to yield 10.45 g of product as a white solid.

Tramadol hydrochloride intermediate

Molecular Weight:153.14
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:153.042593085
Monoisotopic Mass:153.042593085
Topological Polar Surface Area:66
Heavy Atom Count:11
Complexity:143
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes