Methanol → Methyl 2-ethylbenzoate

HRID 1695179Notes

Reaction equation

HRID 1695179 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 88%

Procedure

2-Ethyl-benzoic acid (3.0 g, 20.0 mmol) was dissolved in MeOH (20 mL) and catalytic quantity of sulfuric acid (1 mL) was added. The mixture was refluxed overnight, after that 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 (2.9 g, yield 88%) was used without further purification

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customafter that 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-06f6eb6df7404cfda2c5afc5b1d639fe
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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