3-(2-METHOXY-PHENYL)-PROPIONALDEHYDE

General procedure: Suitable 3-(substituted-phenyl)-propan-1-ol (4a-e, 0.02727 mol)compound was dissolved in DMSO (150 mL) and to the mixture IBX(28 g, 0.02727 mol) was added portion wise during 45 min. Aftercompletion of addition, the reaction mixture was stirred for 2 h. at roomtemperature. After completion of reaction which was monitored by TLChexane/ethyl acetate (8:2), the reaction mixture was poured into water(200 mL). The mixture was filter off; the filter bed was washed withchloroform (200 mL). The filtrate was taken in to a separating funnel, separated the organic layer and the aqueous layer was extracted withchloroform (200 mL). The combined organic layer was washed withwater, brine solution, dried over Na2SO4 and concentrated under vacuum.The crude residue was subjected to column chromatography onsilica gel, using ethyl acetate in hexane, 15percent/85percent (v/v) eluents asmonitored by TLC, pure fractions were combined and concentrated toobtained 3-(substituted-phenyl)-propan-1-al as oily compounds withyields of (5a-e, 73–81percent).The suspension of 2-methoxycinnamaldehyde (1.00 g, 6.17 mmol) and Pd/C (131 mg, 0.20 mmol) werestirred in MeOH (12 mL) at room temperature for 2 h. The reaction mixture was filtered on celite with dichloromethane. The mixture solvent was evaporated under reduced pressure, and the residue was purifiedby column chromatography with hexane/ethyl acetate (3/1, v/v) to obtain 3-(2-methoxyphenyl)propanal.General procedure: In a typical experiment, a solution of PtCl2[(R)-BINAP] (4.5 mg;0.005 mmol) and tin(II) chloride (1.9 mg; 0.01 mmol) in toluene(5 mL) containing styrene derivatives (1a-g, 5a-g) (1.0 mmol) wastransferred under argon into a 100 mL stainless steel autoclave. Thereaction vessel was pressurized to 80 bar total pressure (CO/H2 1:1) and placed in an oil bath of constant temperature. Themixture was stirred with a magnetic stirrer for the given reactiontime. The pressure was monitored throughout the reaction. Aftercooling and venting of the autoclave, the pale yellow solution wasremoved and immediately analyzed by GC-MS and chiral GC.General procedure: In a typical experiment, a solution of PtCl2[(R)-BINAP] (4.5 mg;0.005 mmol) and tin(II) chloride (1.9 mg; 0.01 mmol) in toluene(5 mL) containing styrene derivatives (1a-g, 5a-g) (1.0 mmol) wastransferred under argon into a 100 mL stainless steel autoclave. Thereaction vessel was pressurized to 80 bar total pressure (CO/H2 1:1) and placed in an oil bath of constant temperature. Themixture was stirred with a magnetic stirrer for the given reactiontime. The pressure was monitored throughout the reaction. Aftercooling and venting of the autoclave, the pale yellow solution wasremoved and immediately analyzed by GC-MS and chiral GC.General procedure: To theactivated H-type zeolite (0.10 g) in a 10-mL flask was added abenzene derivative (10mL or 10 g) of a reactant as well as asolvent at the specified reaction temperature. After the mixturewas stirred for more than 10min, acrolein (1.0mmol) wasadded over a period of one minute. After the reaction wascompleted, the reaction vessel was placed in an ice-water bath, and ethanol (5 mL) was added. The mixture was stirred for10min, and then the H-type zeolite was removed by filteringthrough a 1016m sintered glass funnel, washed with ethanol(20 mL) and ethyl acetate (20 mL). To the combined filtrate wasthen added an internal standard substance, and the mixture wasanalyzed by gas chromatography (GC). The reaction yields byGC analysis were calculated based on the amount of the addedacrolein. When a decreased amount (10 or 1.0mmol) of abenzene derivative was used, a benzene derivative in a certainsolvent (10 mL) was added to the activated H-Beta zeolite(0.10 g) in a 10-mL flask. The yields of only 2g and 2h wereobtained by isolation.

Molecular Weight:164.20
XLogP3:2.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:4
Exact Mass:164.083729621
Monoisotopic Mass:164.083729621
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:134
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes