3-Methoxybenzyl alcohol

Colorless to light yellow liqui

3-Methoxybenzyl alcohol is a member of methoxybenzenes.

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: benzaldehyde derivatives (1 mmol) in methanol (15 mL), sodium borohydride (2 mmol) and stirred at room temperature for 1 h. Usual work-up, quantitative yield.General procedure: A mixture of 1a (196 mg, 1 mmol) and 1percentPd/Ni bimetallic catalyst9 (60 mg, 30 wt percent) in MeOH (10 mL) was stirred underH2 at room temperature and atmospheric pressure (on an atmosphericpressure hydrogenation apparatus) until the absorption of hydrogen ceased(3.5 h). After the catalyst was removed off by a magnetic stirring bar, thesolution was evaporated in a vaporator to give the product 2aGeneral procedure: In a round-bottomed flask (10 ml) equipped with a magnetic stirrer, a solution of benzaldehyde (0.106 g, l mmol) and acetophenone (0.120 g, 1 mmol) in H2O (3 mL) was prepared. To this solution, NaBH4(0.047 g, 1.25 mmol) and PhCO2Na (0.138 g, 2 mmol) was added. The mixture was stirred and irradiated with ultrasound waves at room temperature for 60 minutes. TLC monitored the progress of reaction. After 60 min, the reaction mixture was quenched by addition of distilled water (5 ml) and this mixture was then stirred for an additional 1 min. The mixture was extracted with CH2Cl2(5×10 ml) and dried over anhydrous sodium sulfate.Evaporation of the solvent and short column chromatography of the resulting crude material over silicagel by eluent of Hexane/EtOAc: 9/1 affords the pure liquid benzyl alcohol (0.099 g, 92percent) as a sole product of reduction and acetophenone as an intact material (table 2, entry 1)General procedure: To a solution of 3, 4-dimethoxybenzaldehyde (1 g, 6 mmol) in methanol was added NaBH4 (0.27, 7.2 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 4 h, quenched with 3percent aqueous HCl solution, and evaporated to dryness. The residue was extracted with CH2Cl2 and the organic layer was dried with MgSO4. Evaporation of the dried organic layer yielded 0.96g (3, 4-dimethoxyphenyl)methanol (6D0) as a white solid.To a solution of 3-methoxybenzaldehyde (3.11 g, 0.022 mole) in THF (10 mL) and methanol (20 mL), NaBH4 (1.43 g, 0.042 mole) was added portion wise at 0— 10 °C under nitrogen atmosphere. After addition, reaction mixture was stirred at RT for 12 hours. Reaction mixture was concentrated under vacuum and quenched in towater (50 mL). Aqueous layer was extracted with ethyl acetate (50 mL x 3). The organic layer was dried over Na2SO4 and concentrated under vacuum to get (3- methoxy-phenyl)-methanol.Yield: 2.95 g (93 percent); ‘H - NMR (CDC13, 400 MHz) ö ppm: 3.85 (s, 3H), 4.69 - 4.71 (m, 2H), 6.85 - 6.88 (m, 1H), 6.96 - 6.97 (m, 2H), 7.28 - 7.32 (m, 1H).General procedure: Carbonyl substrate, 0.02 mol, was added in portions to a suspension of 0.01 mol NaBH4 in 0.3 mol of the corresponding alcohol solvent, and the mixture was stirred for 2–2.5 h at 20°C. The resulting boron derivatives of benzyl alcohols were decomposed with 10percent aqueous HCl (3.7 mL), and the mixture was stirred for a required time at a required temperature(see Tables 1–5), cooled, and poured into 200 mL of cold water. The products were extracted with diethylether (2 × 40 mL), the combined extracts were washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off on a rotary evaporator, and the residue was analyzed by General procedure: Benzaldehyde (1 g, 9.5 mmol, 1 equiv) was dissolved in 38 mL (1:1 IPA/ H2O), (0.25 M). Sodium dithionite (7.5 g, 43 mmol, 4.5 equiv) and NaHCO3 (1.6 g, 19 mmol, 2 equiv) was dissolved in water (43 mL, [1 M]) and added to the aldehyde. The mixture was refluxed for 12 hours under argon. The solution was allowed to cool to room temperature and the products were extracted using EtOAc (3 × 50 mL). This was dried using Na2SO4, filtered and dried under vacuum with a yield of 0.95 g (92percent). For entry 1.15 the compound was neutralized with 1 M HCl and extracted with EtOAc (3 × 50 mL) and washed with water (3 × 50 mL) the organic extracts were combined and dried using Na2SO4. The solvent was evaporated in vacuo and the resulting residue purified using column chromatography. Unless specified a 3:1 EtOAc/hexane eluent was used for chromatographic purification [1-3].General procedure: A mixture of an appropriate carbonyl compound (1 mmol), NaBH4 (1 mmol) and nanocatalyst (2 mg, 0.01 molpercent) was stirred for5 min, followed by addition of distilled water (3 mL). The reactionprogress was monitored by TLC or GC. After completion of thereaction the catalyst was separated by simplefiltration and theresidue was extracted with ethyl acetate and washed with water(5–7 times). The organic layer was dried over MgSO4, filtered off, evaporated to dryness under reduced pressure to give thecorresponding hydroxyl compounds.General procedure: 0.05 g 5 wt.percent Pt catalyst was pretreated in a hydrogen flow at 673 K for 2 h before use. The catalyst was then mixed with 20 mL solvent and transferred to a 100 mL autoclave. The hydrogenation reaction began at a designated temperature after 4.0 MPa hydrogen was introduced into the autoclave. The reaction was stopped after an allotted period and the products were analyzed by GC–FID (GC-2014, Shimadzu Co.) equipped with a capillary column (DM-WAX, 30 m × 0.32 mm × 0.25 μm).

This product is a diuretic. Carbonic anhydrase inhibitors, after taking, inhibit carbonic anhydrase in renal tubular epithelial cells, so that the formation of H2CO3 is reduced, and the production of H+ decreases accordingly. Therefore, the exchange of H+ and Na+ is greatly slowed down. As a result, the excretion of HCO3-, Na+, K+ increases, and the amount of urine increases. The product can still inhibit the secretion process of aqueous humor, and lower the intraocular pressure. It is used to treat glaucoma and mild cardiac edema.

Molecular Weight:138.16
XLogP3:1.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:138.068079557
Monoisotopic Mass:138.068079557
Topological Polar Surface Area:29.5
Heavy Atom Count:10
Complexity:93.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes