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  (Organic Chemistry)

Alcohol to Acid



Example 1

To a solution of the SM (8.34 g, 18.15 mmol) in ACN (100 mL) was added NMO (8.51 g, 72.6 mmol) and TPAP (0.51 g, 1.45 mmol) in three portions. The resulting mixture was stirred at RT for 4 h. Then IPA (20 mL) was added and the mixture was stirred overnight. The mixture was concentrated in vacuo and the residue was partitioned between EtOAc (200 mL) and 1N HCl (80 mL). The layers were separated and the org layer was washed with brine, dried (Na2SO4), and concentrated to provide the product. [8.0 g, 16.90 mmol]

[Patent Reference: WO2016085780, page 53, (6.8 MB)]