Acetyl chloride → Methyl 2-methyl-5-nitrobenzoate

HRID 1012637Notes

Reaction equation

HRID 1012637 reaction equation
[C:1](Cl)(=O)C.[CH3:5][C:6]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]>CO>[CH3:1][O:9][C:8](=[O:10])[C:7]1[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:6]=1[CH3:5]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 5196832-Methyl-5-nitrobenzoic acid

Product 1

HCID 4377758Methyl 2-methyl-5-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (15 ml) was added to MeOH (500 ml) at room temperature. After 10 min, 2-methyl-5-nitro-benzoic acid (25.00 g, 138.00 mmol) was added. The reaction solution was heated for reflux for 18 h. The solution was then concentrated in vacuo. The residue was dissolved in diethyl ether and washed with H2O and saturated aqueous solution of NaHCO3 respectively. The organic phase was dried over MgSO4 and concentrated in vacuo to provide the title compound as a white solid.

Workup

  1. temperatureThe reaction solution was heated
  2. temperaturefor reflux for 18 h
  3. concentrationThe solution was then concentrated in vacuo
  4. dissolutionThe residue was dissolved in diethyl ether
  5. washwashed with H2O and saturated aqueous solution of NaHCO3 respectively
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5a31953db7f5446c963780f572a4d6ea
Source dataset
uspto-grants-2011_07
Patent number
US07977387B2

Reaction notes

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