Methanol → Methyl 2-ethylbenzoate

HRID 461696

Reaction equation

HRID 461696 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>>[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH3:17])=[O:6])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 341702-Ethylbenzoic acid

Product 1

HCID 583295Methyl 2-ethylbenzoateYield 86%

Procedure

A solution of 11.8 g. (0.076 mole) of 2-ethylbenzoic acid in 25 ml. of absolute methanol is treated cautiously with 2.5 ml. of concentrated sulfuric acid and heated to reflux. After 4 hours, the mixture is poured onto ice and the oily product is extracted into ether. Evaporation of the washed (water, 5% aqueous sodium bicarbonate and water) and dried extract under reduced pressure leaves methyl 2-ethylbenzoate as the residual colorless oil in a yield of 86%.

Workup

  1. additionthe mixture is poured onto ice
  2. extractionthe oily product is extracted into ether
  3. customEvaporation of the
  4. washwashed (water, 5% aqueous sodium bicarbonate and water)
  5. customdried
  6. extractionextract under reduced pressure

Sources & evidence

ORD record
ord-d0774594c4754049864648af9a863140
Source dataset
uspto-grants-1977_12
Patent number
US04064139

Linked notes

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