Triacetoxyperiodinane → 2-Methoxy-4-(2-oxopropyl)benzonitrile

To a stirred solution of 4-(2-hydroxypropyl)-2-methoxybenzonitrile (1.45 g, 7.6 mmol) in dry CH2Cl2 (30 mL) at 0° C. was added Dess-Martin periodinane (4.2 g, 9.8 mmol) in one portion. The mixture was stirred for 12 h at RT and quenched with a 1:1 mixture of saturated Na2S2O3 (20 mL) and saturated NaHCO3 (20 mL). The resulting mixture was diluted with CH2Cl2 (50 mL) and the layers were separated. The aqueous phase was extracted with CH2Cl2 (2×50 mL). The combined organic phases were washed with brine, dried (Na2SO4), and concentrated in vacuo to give 2-methoxy-4-(2-oxopropyl)benzonitrile as an oil. The crude residue was used in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.55 (dd, 1H, J=1.6 Hz), 6.87 (d, 1H, J=7.8 Hz), 6.83 (s, 1H), 3.96 (s, 3H), 3.79 (s, 2H), 2.25 (s, 3H).

1. customquenched with a 1:1 mixture of saturated Na2S2O3 (20 mL) and saturated NaHCO3 (20 mL)
2. additionThe resulting mixture was diluted with CH2Cl2 (50 mL)
3. customthe layers were separated
4. extractionThe aqueous phase was extracted with CH2Cl2 (2×50 mL)
5. washThe combined organic phases were washed with brine
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo

ORD record

ord-dc8b71f0c42046569b2764b02d578720

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073882B2