Diethyl Ether → Benzoic acid, 2,6-dinitro-

Potassium nitrosodisulfonate (13.4 g, 50 mmol) in 500 mL of 4% aqueous sodium carbonate solution is added to a 1 L Erlenmeyer flask equipped with a large magnetic stir bar. Then, with stirring, a solution of 2,6-dinitrophenylacetonitrile (2.07 g, 10 mmol) in 50 mL of acetonitrile is gradually added over the course of 20 min at ambient temperature. Stirring continued for 3.5 h. Three separate sequential portions of additional potassium nitrosodisulfonate (2.6 g, 9.7 mmol) are added at time points 0.5 h, 1 h and 2 h, and stirred for 3.5 h in total. Diethyl ether (100 mL) is then added to the reaction and is stirred at ambient temperature for 1 h. The layers are separated and the ether layer is discarded. The aqueous layer is cautiously acidified with cone. HCl to pH 2, and 150 mL of diethyl ether is added to the mixture with stirring at ambient temperature for 0.5 h. The layers are separated and the aqueous layer is further extracted with 100 mL and 50 mL portions of diethyl ether. The combined ether layers are dried over magnesium sulfate, filtered and evaporated to afford 1.91 g (90% yield) of the 2,6-dinitrobenzoic acid.

1. customequipped with a large magnetic stir bar
2. stirringStirring
3. additionare added at time points 0.5 h, 1 h and 2 h
4. stirringstirred for 3.5 h in total
5. stirringis stirred at ambient temperature for 1 h
6. customThe layers are separated
7. additionHCl to pH 2, and 150 mL of diethyl ether is added to the mixture
8. stirringwith stirring at ambient temperature for 0.5 h
9. customThe layers are separated
10. extractionthe aqueous layer is further extracted with 100 mL and 50 mL portions of diethyl ether
11. dry with materialThe combined ether layers are dried over magnesium sulfate
12. filtrationfiltered
13. customevaporated

ORD record

ord-51a2d9e37c62421786ce3298e2abdc6d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710260B2