Methanol → Methyl 3-ethylbenzoate

HRID 2045837

Reaction equation

HRID 2045837 reaction equation
OS(O)(=O)=O.[CH2:6]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([OH:13])=[O:12])[CH3:7].[CH3:17]O>O>[CH2:6]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([O:13][CH3:17])=[O:12])[CH3:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 96207Benzoic acid, 3-ethyl-

Product 1

HCID 12430992Methyl 3-ethylbenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated H2SO4 (1.0 mL) was added to a solution of 3-ethylbenzoic acid (500 mg, 3.33 mmol) in MeOH (10 mL). The mixture was heated at reflux for 18 h then cooled to room temperature. The mixture was diluted with water (50 mL) and extracted with Et2O (3×100 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo. Purification of the crude residue by chromatography on silica gel (hexanes→20% EtOAc/hexanes, gradient) afforded 500 mg (91%) of methyl 3-ethylbenzoate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. extractionextracted with Et2O (3×100 mL)
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude residue by chromatography on silica gel (hexanes→20% EtOAc/hexanes, gradient)

Sources & evidence

ORD record
ord-2d3725fd1f9a4187a86fa47cc24da609
Source dataset
uspto-grants-2013_11
Patent number
US08592413B2

Linked notes

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