Methanol → Methyl 3-methoxybenzoate

HRID 2205127Notes

Reaction equation

HRID 2205127 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].OS(O)(=O)=O.[CH3:17]O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:8][CH3:17])=[O:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 114613-Methoxybenzoic Acid

Product 1

HCID 79332Methyl 3-methoxybenzoateYield 96%

Procedure

A solution of 3-methoxybenzoic acid (20 g, 131.58 mmol, 1.00 equiv) in MeOH (100 mL) and H2SO4 (13 g, 130.00 mmol, 1.00 equiv, 98%) was allowed to react, with stirring in a 250-mL round-bottom flask, overnight under reflux. The reaction was quenched by the addition of 100 mL of water/ice, extracted with 3×100 mL of dichloromethane, and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum yielding 21 g (96%) of methyl 3-methoxybenzoate as yellow oil.

Workup

  1. customto react
  2. temperatureunder reflux
  3. customThe reaction was quenched by the addition of 100 mL of water/ice
  4. extractionextracted with 3×100 mL of dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe solids were filtered out
  7. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-a3406af7ae0f442ea8719a69e6604157
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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