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X. Xia et al.
Letter
Synlett
References and Notes
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(21) Wacker Oxidation of Olefins; General Procedure
5 wt% Pd0/C (0.05 mmol) and 70 wt% H2SO4 (0.2 mmol) were
added to a solution of the appropriate styrene (1 mmol) in
MeCN (5 mL), and the mixture was stirred for about 15 min at
r.t. Then, 30 wt% H2O2 (6 mmol) was added dropwise, and the
mixture was heated at 65 °C until the reaction was complete
(TLC). The Pd0/C was removed by centrifugation and the
remaining mixture was partitioned between H2O and EtOAc.
The layers were separated, and the organic layer was washed
with H2O, dried (Na2SO4), filtered, and concentrated under
reduced pressure. The crude residue was purified by column
chromatography.
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Acetophenone (Table 2, Entry 16)
Light-yellow liquid; yield: 1.03 g (90%). 1H NMR (300 MHz,
CDCl3): δ = 7.96 (d, J = 7.1 Hz, 2 H), 7.57 (t, J = 7.3 Hz, 1 H), 7.47
(t, J = 7.4 Hz, 2 H), 2.61 (s, 3 H). 13C NMR (75 MHz, CDCl3):
δ = 198.1, 136.9, 133.0, 128.4, 128.2, 26.5.
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, A–D