Methanol → Acetophenone

Wacker-Tsuji oxidation of styrene in a PDMS thimble. A PDMS thimble containing PdCl2 (0.025 g, 0.141 mmol) and CuCl (0.282 g, 2.82 mmol) was placed in a 2-necked Schlenk flask with a stir bar. MeOH (1.98 mL) and H2O (0.28 mL) were added to the inside of the PDMS thimble and the flask was capped with a rubber septum. A balloon filled with O2 was affixed to the septum and the reaction mixture was stirred at room temperature for 1 hour. Styrene (0.323 mL, 2.82 mmol) was added to the reaction mixture and allowed to stir under an O2 atmosphere for 24 hours. The PDMS thimble was swelled with hexane (2×25 mL) for 12 hours with a stir bar on the exterior of the PDMS thimble. The hexane extracts were combined and the solvent was removed in vacuo. A 1H NMR spectrograph was recorded in CDCl3 to determine quantitative conversion of the styrene to the following products: 89% ketone, 1% aldehyde, 8% acetal, and 2% ketal. Acetophenone (0.249 g, 73% yield) was isolated as a clear liquid by column chromatography using hexanes/EtOAc (95/5). NMR spectra matched those reported in the literature.13 1H NMR (300 MHz, CDCl3, δ): 7.94 (m, 2H), 7.54 (m, 1H), 7.45 (m, 2H), 2.58 (s, 3H). 13C NMR (75.48 MHz; CDCl3, δ): 197.9, 137.0, 132.9, 128.4, 128.1 and 26.4.

1. customwas placed in a 2-necked Schlenk flask with a stir bar
2. customthe flask was capped with a rubber septum
3. stirringto stir under an O2 atmosphere for 24 hours
4. customthe solvent was removed in vacuo

ORD record

ord-8cd8a5545fea4d10bfc2d753d0bad86e

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08227635B2