Methanol → Methyl 4-methoxy-2-nitrobenzoate

HRID 1914676Notes

Reaction equation

HRID 1914676 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.S(Cl)(Cl)=O.[CH3:19]O>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH3:19])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2886574-Methoxy-2-nitrobenzoic acid

Product 1

HCID 17733355Methyl 4-methoxy-2-nitrobenzoateYield 85%

Procedure

To a solution of 4-methoxy-2-nitrobenzoic acid (12 g; 61 mmol; 1 eq; commercially available from Aldrich) in MeOH (200 mL) is added thionyl chloride (13 mL, 178 mmol, 2.9 eq) and the mixture is stirred at room temperature for 15 h. The solvent is removed under vacuum and the residue is diluted with EtOAc (150 mL) and washed with a 10% aqueous solution of sodium bicarbonate, water, and then dried over MgSO4. The solvent is removed under reduced pressure to afford 11 g (85%) of the title compound as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.81-7.79 (m, 1H), 7.27-7.25 (m, 1H), 7.13-7.11 (m, 1H), 3.92 (s, 3H), 3.89 (s, 3H).

Workup

  1. customThe solvent is removed under vacuum
  2. additionthe residue is diluted with EtOAc (150 mL)
  3. washwashed with a 10% aqueous solution of sodium bicarbonate, water
  4. dry with materialdried over MgSO4
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-35b1aafb22d34ceca21d81ec9dbf0bdd
Source dataset
uspto-grants-2013_12
Patent number
US08614215B2

Reaction notes

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