Methanol → Methyl 4-chloro-3-nitrobenzoate

HRID 538599Notes

Reaction equation

HRID 538599 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].OS(O)(=O)=O.[CH3:19]O>>[CH3:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 73204-Chloro-3-nitrobenzoic acid

Product 1

HCID 735797Methyl 4-chloro-3-nitrobenzoateYield 94%

Conditions

Temperature
70 °C

Procedure

To a Solution of 4-chloro-3-nitrobenzoic acid (5.0 g, 24.81 mmol) in 50 ml of methanol was added H2SO4 (2 ml, 37.02 mmol) and the reaction mixture was heated at 70° C. for 5 h. After completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure. Water (50 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was, dried (Na2SO4), filtered and concentrated to give the desired product (5.04 g, 94%).

Workup

  1. customAfter completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure
  2. additionWater (50 mL) was added
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59e17a11bb444eb0adb5f43496651bba
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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