Nitric Acid → N-[4-(2,2-dimethylpropyl)phenyl]acetamide

To a solution of neopentylbenzene (9.20 g, 62 mmol) in acetic anhydride (30 mL) cooled in an ice bath was slowly added a solution of nitric acid (3.5 mL, 83 mmol) in acetic anhydride (10 mL). The reaction was allowed to warm to room temperature for 18 hours. The yellow reaction mixture was added to ice water and extracted with diethylether (3×). The organic layers were combined, washed with brine, dried over anhydrous magnesium sulphate, filtered, and concentrated in vacuo. This provided a 1:1 mixture of ortho and para nitro substituted compounds as a yellow solid. To this yellow solid dissolved in methanol (100 mL) was added acetic anhydride (8.4 mL, 89 mmol) and 10% palladium on carbon (700 mg, 7 mmol) and the reaction mixture hydrogenated at a pressure of 40 psi for 3 hours. The reaction was filtered through celite, concentrated in vacuo, and purified by silica gel column chromatography eluting with a 0-50% ethyl acetate/hexanes gradient. This provided the title compound (2.79 g, 22%) as a white solid.

1. extractionextracted with diethylether (3×)
2. washwashed with brine
3. dry with materialdried over anhydrous magnesium sulphate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThis provided
7. additiona 1:1 mixture of ortho and para nitro substituted compounds as a yellow solid
8. filtrationThe reaction was filtered through celite
9. concentrationconcentrated in vacuo
10. custompurified by silica gel column chromatography
11. washeluting with a 0-50% ethyl acetate/hexanes gradient

ORD record

ord-a5956302f971424e9e7e31976332d748

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927587B2