Acetyl chloride → Benzoic acid, 3-methyl-2-nitro-, methyl ester

HRID 655928Notes

Reaction equation

HRID 655928 reaction equation
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:14](Cl)(C)=O>CO.CCOC(C)=O>[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:14])=[O:6]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 215753-Methyl-2-nitrobenzoic acid

Product 1

HCID 79621Benzoic acid, 3-methyl-2-nitro-, methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-methyl-2-nitro-benzoic acid (1.0 eq.) in MeOH (0.4 M) at 0° C. was added dropwise AcCl (3.0 eq.). The reaction mixture was stirred for 20 hr at reflux. The solvent was reduced in vacuo and the residue was dissolved in EtOAc and washed several times with sat. aq. NaHCO3 solution, brine and dried (Na2SO4). Evaporation of the solvent gave (A1) as a white solid which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3, 300K) δ 7.86 (1H, d, J=7.5 Hz), 7.53−7.42 (2H, m), 3.89 (3H, s), 2.36 (3H, s). MS (ES) C9H9NO4 requires: 195. Found: 218 (M+Na)+.

Workup

  1. temperatureat reflux
  2. washwashed several times with sat. aq. NaHCO3 solution, brine
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ceaa3dd3b41742149a7d0b466ad082e4
Source dataset
uspto-grants-2011_12
Patent number
US08071623B2

Reaction notes

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