Methanol → Methyl 4-chloro-2-methyl-3-nitrobenzoate

HRID 1161184Notes

Reaction equation

HRID 1161184 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([CH3:11])[C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15]O.S(Cl)(Cl)=O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:15])=[O:7])=[C:4]([CH3:11])[C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 107039094-Chloro-2-methyl-3-nitrobenzoic acid

Product 1

HCID 10657064Methyl 4-chloro-2-methyl-3-nitrobenzoate

Conditions

Temperature
75 °C

Procedure

A round bottom flask was charged with 4-chloro-2-methyl-3-nitrobenzoic acid (11.00 g, 0.05102 mol) and methanol (110 mL, 2.7 mol) and thionyl chloride (4.5 mL, 0.061 mol) was added at 0° C. and the reaction heated at 75° C. for 3 hours. The solvent was removed under reduced pressure and the residue dissolved in ethyl acetate (300 mL) and washed with aqueous sodium bicarbonate, water and brine. The organic extracts were dried over sodium sulfate and the solvent removed to recover the esters. MS m/z=230.3 (M+H).

Workup

  1. additionwas added at 0° C.
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue dissolved in ethyl acetate (300 mL)
  4. washwashed with aqueous sodium bicarbonate, water and brine
  5. dry with materialThe organic extracts were dried over sodium sulfate
  6. customthe solvent removed
  7. customto recover the esters

Sources & evidence

ORD record
ord-c02916a712bf4fda96931872554bdf30
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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