Iodine → 4-Chloro-2-methoxybenzaldehyde

Temperature

5 °C

Following the general method of R. A. Miller and R. S. Hoerrner, Org. Lett., 5, 285 (2003), a solution of 2.5 g (14.1 mmol based on 97% purity) of 4-chloro-2-methoxybenzyl alcohol in 35 mL of toluene was treated with 35 mL of water and 3.54 g (42.3 mmol) of sodium bicarbonate. The resulting two-phase mixture was stirred at ambient temperature as 7.2 g (28.2 mmol) of iodine was added, followed by 0.223 g (1.41 mmol) of 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical (TEMPO). After 3 days, the dark mixture was cooled to 5° C. and quenched by addition of a solution of 1.8 g of sodium sulfite in 18 mL of water. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with brine. The organic phase was then dried over anhydrous sodium sulfate. The supernatant was concentrated to a volume of approximately 5 mL and kept at 5° C. for 1 h. The solid that separated was collected on a filter, washed twice with small volumes of cold toluene, and dried in vacuo to yield the title compound as a white solid. LC-MS 171 (M+1).

1. additionwas added
2. customquenched by addition of a solution of 1.8 g of sodium sulfite in 18 mL of water
3. customThe mixture was partitioned between ethyl acetate and water
4. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
5. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
6. concentrationThe supernatant was concentrated to a volume of approximately 5 mL
7. waitkept at 5° C. for 1 h
8. customThe solid that separated
9. customwas collected on a filter
10. washwashed twice with small volumes of cold toluene
11. customdried in vacuo

ORD record

ord-24ca848482da47aba32bbde909136726

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956061B2