Methanol → Methyl 3,5-dimethyl-4-nitrobenzoate

HRID 239921Notes

Reaction equation

HRID 239921 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:14])[C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:19]O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:14])[C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH3:19])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2494133,5-Dimethyl-4-nitrobenzoic acid

Product 1

HCID 22998442Methyl 3,5-dimethyl-4-nitrobenzoateYield 98.3%

Conditions

Temperature
80 °C

Procedure

To a solution of 3,5-dimethyl-4-nitro-benzoic acid (10.0 g, 0.0512 mol) in MeOH (150 mL) is added thionyl chloride (10 ml) at 0° C. and the reaction is heated to 80° C. After 16 h, the reaction mixture is cooled to room temperature and solvent is removed under reduced pressure. The residue is diluted with water (50 ml) and basified with saturated NaHCO3 solution to pH 7-8 and extracted with EtOAc (2×120 mL). The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to afford the title compound as a light yellow solid (10.71 g, 98.3%). 1H NMR (400 MHz, DMSO): δ 7.83 (s, 2H), 3.88 (s, 3H), 2.30 (s, 6H).

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. customsolvent is removed under reduced pressure
  3. additionThe residue is diluted with water (50 ml)
  4. extractionextracted with EtOAc (2×120 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-d8a315d745504457bb96a8f59c0c67d3
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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