Methanol → Methyl 2,5-dimethyl-4-nitrobenzoate

HRID 1094945Notes

Reaction equation

HRID 1094945 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([CH3:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:19]O>>[CH3:1][C:2]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([CH3:14])=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 2494162,5-Dimethyl-4-nitrobenzoic acid

Product 1

HCID 57461068Methyl 2,5-dimethyl-4-nitrobenzoate

Procedure

To a stirred solution of 2,5-dimethyl-4-nitrobenzoic acid (480 mg, 2.4 mmol) in dry methanol (8.2 mL) at 0° C. under dry nitrogen was added thionyl chloride (0.538 mL, 7.38 mmol). The resulting mixture as allowed to warm to room temperature and stirred for about 7 hours. Additional thionyl chloride (0.300 mL) was added and stirring was continued at room temperature overnight. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate. This solution was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide methyl 2,5-dimethyl-4-nitrobenzoate (578 mg) as a pale yellow solid. HPLC (10-70) Rt=4.61; NMR (300 MHz, CDCl3) δ 2.57 (s, 3H), 2.61 (s, 3H), 3.94 (s, 3H), 7.82 (s, 1H), 7.87 (s, 1H).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThis solution was washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e4098bfdd5b4295b12d65c44933a79b
Source dataset
uspto-grants-2012_03
Patent number
US08134006B2

Reaction notes

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