Acetic Acid → 5-Methoxy-2-methyl-4-nitrobenzoic acid

HRID 2406303Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[CH:5][C:6](C)=[C:7]([CH:10]=1)C#N.C(Cl)Cl.[CH3:18][C:19]([OH:21])=[O:20]>O.S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[C:4]([N+:12]([O-:14])=[O:13])=[CH:5][C:6]([CH3:7])=[C:18]([CH:10]=1)[C:19]([OH:21])=[O:20]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-methoxy-2-methyl-4-nitrobenzonitrile (2.0 g, 10.4 mmol) in AcOH (20 mL), water (20 mL) and conc. sulfuric acid (20 mL) was heated to 120° C. for 10 h. Water (100 mL) and DCM (100 mL) were added and the mixture was passed through a hydrophobic frit. The solvent was removed in vacuo to give 5-methoxy-2-methyl-4-nitrobenzoic acid (2.0 g, 91%) as an off-white solid. LCMS (10 cm_ESCI_Formic_MeCN): [M−H]−=210 at 3.37 min. 1H NMR (400 MHz, CDCl3): δ 7.75 (s, 1H), 7.70 (s, 1H), 3.99 (s, 3H), 2.62 (s, 3H).

Workup

customThe solvent was removed in vacuo

Sources & evidence

ORD record: ord-8d6eca6fab6c47f48dad38d0ac1fbf5f
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809331B2

Reaction notes

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