Methyl 4-methoxyphenylacetate → 4-Methoxyphenylacetaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (4-Methoxy-phenyl)-acetic acid methyl ester (18.0 g, 100 mmol) in anhydrous toluene (200 mL) cooled to −78° C. under N2 was added diisobutylaluminum hydride (DIBAL, 1.0 M in toluene, 150 mL, 150 mmol) over a period of 10-15 minutes. The mixture was stirred at −78° C. for an additional 2 h. The reaction was quenched by the slow addition of MeOH, followed by the introduction of 10% Rochelle's Salt. The suspension was diluted with EtOAc and stirred at room temperature for 1 h. The EtOAc layer was set aside and the aqueous layer was extracted with EtOAc(2×). The combined organic layers were combined and dried over Na2SO4 and filtered. The solution was concentrated under vacuum to yield 12.0 g (100%) of the title aldehyde as a yellow viscous semisolid, which was used in the next step without purification. LC/MS (APCI, ES, M+H=151).

Provenance & Evidence