4-Formyl-3-methoxybenzonitrile

79 g (370 mmol) of sodium metaperiodate are added in portions to a vigorously stirred solution of 48 g (185 mmol) of tert-butyl (2E)-3-(4-cyano-2-methoxyphenyl)acrylate, 207 mg (0.81 mmol) of osmium tetroxide and 1.4 g (6.14 mmol) of benzyltriethylammonium chloride in 750 ml of water/THF (2:1), keeping the reaction temperature below 30° C. 79 g (370 mmol) of sodium metaperiodate are added in portions to a vigorously stirred solution of 48 g (185 mmol) of tert-butyl (2E)-3-(4-cyano-2-methoxyphenyl)acrylate, 207 mg (0.81 mmol) of osmium tetroxide and 1.4 g (6.14 mmol) of benzyltriethylammonium chloride in 750 ml of water/THF (2:1), keeping the reaction temperature below 30° C. The solution is stirred further at RT for 1 h. Water (2000 ml) is added, and the mixture is then filtered. The remaining solid is dissolved in ethyl acetate, and the solution is washed with saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated. The residue is stirred with petroleum ether. 21.18 g (71percent of theory) of the title compound are obtained as a white solid.LC-MS (Method 1): Ra): trifluoromethanesulfonic anhydride, pyridine, 0° C.-->RT, 30 min; b): tert-butyl acrylate, bis(triphenylphosphine)dichloropalladium(II), DMF, 120° C., 24 h; c): cat. osmium tetroxide, cat. benzyltriethylammonium chloride, sodium periodate, THF/water, 20-25° C., 2 h; Example 15A While maintaining the reaction temperature below 30 , sodium meta-periodate flops date 79 g (370 mmol) of water / THF (2: 1) of 750 mL tert-butyl(2E)-3-(4-cyano-2-methoxyphenyl)acrylate 48 g (185 mmol), osmium tetroxide 207 mg (0.81 mmol) was added little by little, and the strongly stirred solution of benzyl triethyl ammonium chloride, 1.4 g (6.14 mmol). At room temperature, the solution Stirred for 1 hour. After addition of water (2000 ml), the mixture was filtered. The remaining solid in ethyl acetate Was dissolved, the solution was washed with a saturated aqueous sodium chloride solution. When drying the organic phase over magnesium sulfate and concentrated It turned on. The residue was stirred with petroleum ether. (71percent of theory) the title compound was obtained as a white solid 21.18 g All.719 g (3.34 mol) of 4-bromo-2-methoxybenzaldehyde (XVI) as a solution in 4.5 l of DMF were charged with 313 g (0.74 mol) of potassium hexacyanoferrate (K719 g (3.34 mol) of 4-bromo-2-methoxybenzaldehyde (XVI) as a solution in 4.5 l of DMF were charged with 313 g (0.74 mol) of potassium hexacyanoferrate (K719 g (3.34 mol) of 4-bromo-2-methoxybenzaldehyde (XVI) as a solution in 4.5 l of DMF are charged with 313 g (0.74 mol) of potassium hexacyanoferrate (-K4-Cyano-2-methoxybenzaldehyde (44f). Thionyl chloride (50 ml) was added to 2-methoxy-4-cyano benzoic acid (Tetrahedron Letters, 1986, 27(49), 5997-6000) (8 g, 45.2 mmol) in dichloromethane (70 ml) and the solution was refluxed for 5 h. After cooling to room temperature, the solvent was removed under reduced pressure. The crude benzoyl chloride was dissolved in diglime (120 ml), cooled at -78° C. and 1M lithium tritertbutoxyaluminium hydride in THF (46 ml, 46 mmol) was added dropwise in 3 h. Stirring was continued for 30 min at -78° C. then the reaction was allowed to reach 0° C. and quenched with water (15 ml) and 2N NaOH (15 ml). The reaction mixture was stirred for 1 h, filtered and the organic phase was removed under reduced pressure. The crude residue was purified by column chromatography eluting with n-hexane/ethyl acetate 80:20 to give 4 g of the title compound (yield 55percent) as a yellow powder, mp=112-114° C. [0187] 1H-NMR (CDCl3) δ=10.5 (s, 1H); 7.93 (d, 1H); 7.30 (d, 1H); 7.16 (s, 1H); 4.01 (s, 3H).A four-neck reaction flask was charged with 128.7 g of 4-hydroxymethyl-3-methoxybenzonitrile (IV) (0.788 mol), 205.6 g of manganese dioxide (2.364 mol) and 1600 g of dichloromethane, and heated to 39°C. The reaction was refluxed for about 8 hours. The reaction was completed. The reaction was cooled to room temperature and filtered. The filter cake was washed well with dichloromethane. The filtrate was concentrated to give a crude product. The crude product was mixed with 80 g of dichloromethane, 80 g of ethanol, and 240 g of petroleum ether. Recrystallization gave 53 g of 2-methoxy-4-cyanobenzaldehyde (V) in 42percent yield.

Molecular Weight:161.16
XLogP3:1.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:161.047678466
Monoisotopic Mass:161.047678466
Topological Polar Surface Area:50.1
Heavy Atom Count:12
Complexity:206
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes