Methanol → Methyl 2-ethylbenzoate

HRID 1695177Notes

Reaction equation

HRID 1695177 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[CH3:2].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 341702-Ethylbenzoic acid

Product 1

HCID 583295Methyl 2-ethylbenzoateYield 96%

Procedure

2-Ethyl-benzoic acid (3.0 g, 17.6 mmol) was dissolved in MeOH (20 mL) and sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after which the solvent was evaporated under reduced pressure; the crude was dissolved in DCM and washed with saturated Na2CO3 to basic pH. The organic phase was dried and evaporated under reduced pressure, and the product (3.1 g, yield 96%) was used without further purification.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customafter which the solvent was evaporated under reduced pressure
  3. dissolutionthe crude was dissolved in DCM
  4. washwashed with saturated Na2CO3 to basic pH
  5. customThe organic phase was dried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a6e6903228d344f494c51a1d71ff13dd
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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