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

HRID 2401465Notes

Reaction equation

HRID 2401465 reaction equation
[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5](C)=[C:6]([CH:9]=1)C#N.[CH3:14][C:15]([OH:17])=[O:16]>O.S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([CH3:6])=[C:14]([CH:9]=1)[C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 102417995-Chloro-2-methyl-4-nitrobenzonitrile

Product 1

HCID 715128585-Chloro-2-methyl-4-nitrobenzoic acidYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-methyl-4-nitrobenzonitrile (1 g, 5 mmol) in AcOH (10 mL), water (10 mL) and conc. sulphuric acid (10 mL) was heated to 120° C. for 5 h. Water (100 mL) was added and the solid was removed by filtration and dried to give 5-chloro-2-methyl-4-nitrobenzoic acid (905 mg, 84%) as an off-white solid. LCMS (10 cm_ESCI_Bicarb_MeCN): [M−H]−=214 at 2.12 min. 1H NMR (400 MHz, CDCl3): δ 8.22 (s, 1H), 7.76 (s, 1H), 2.70 (s, 3H).

Workup

  1. customthe solid was removed by filtration
  2. customdried

Sources & evidence

ORD record
ord-4c4ea3b5f4c04bfba501b297147f50a8
Source dataset
uspto-grants-2014_08
Patent number
US08796296B2

Reaction notes

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