3-Methoxy-4-methylbenzaldehyde

solid

Dess-Martin periodinane (3gm, 7.07 mmol) was added to (3-methoxy-4- methylphenyl)methanol (lgm, 6.57 mmol) in CHTo a solution of the above obtained (3-methoxy-4-methylphenyl) methanol (0.38 g, 2.5 mmol) in dichloromethane (30 mL) was added pyridinium chlorochromate , PCC) (0.62 g, 2.8 mmol) at 0°C. The reaction temperature is raised to room temperature, stirred for 2 hours, filtered through celite, and concentrated under reduced pressure. (56percent yield)General procedure: To a solution of the hydroxy-methylbenzaldehyde (34 mg, 0.25 mmol) in anhydrous DMF (6.0 mL), K2CO3 (35 mg, 0.25 mmol) was added and the mixture was stirred at room temperaturefor 30 minutes. Then, methyl iodide (30 μL, 68 mg, 0.5 mmol) was added and the reaction was stirred at room temperatureovernight. The reaction was quenched by the additionof distilled water, and the aqueous phase was extracted threetimes with ethyl acetate. The combined organic phases weredried with MgSO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel.A mixture of Step 1 : Preparation of 2-methoxy-l-methyl-4-| 2-nitroprop-l -enyl| benzene A mixture of 3-methoxy-4-methyl-benzaidehyde (20 g, 133 mmol), nitroethane (250 g, 3.3 moi) and lLOAc (5 1 g, 665 mmol ) was heated at 1 10 C for 2 hours. After being cooled to room temperature, the mixture was poured into ice-water ( 1000 mL) and then extracted with ethyl acetate (400 mL x 3). The combined organic layers were washed with water (400 mL) and brine (400 mL), and then dried over anhydrous ai-SO-t and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography to afford 2-mcthoxy- 1 -methyl-4-[2-nitraprop- 1 -enyl (benzene as a solid ( 1 0 g).At -78 C, CH3MgCl (2.0 mL, 3.0 M in THF, 6.0 mmol, 1.2 equivalents) was slowly added to wherein the compound of Formula I is selected from the group consisting of ... 2-methoxy-3-methylbenzaldehyde; 2-ethoxy-3-methylbenzaldehyde; 2-propoxy-3-methylbenzaldehyde; 2-isopropoxy-3-methylbenzaldehyde; 13(5)

Molecular Weight:150.17
XLogP3:2.3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:150.068079557
Monoisotopic Mass:150.068079557
Topological Polar Surface Area:26.3
Heavy Atom Count:11
Complexity:134
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes