Ethanol → Ethyl [4-(methylsulfanyl)phenyl]acetate

HRID 2229145Notes

Reaction equation

HRID 2229145 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([O:12][CH2:18][CH3:19])=[O:11])=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 49839124-(Methylthio)phenylacetic acid

Product 1

HCID 10512649Ethyl [4-(methylsulfanyl)phenyl]acetateYield 96%

Procedure

To a solution of 4-methylthiophenylacetic acid (1.0 g, 5.48 mmol) in 55 mL of ethanol was slowly added a catalytic amount of concentrated sulfuric acid. The mixture was stirred at room temperature overnight and then concentrated at reduced pressure. The residue was partitioned between methylene chloride and sodium bicarbonate. The organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated to yield 1.1 g of a colorless oil (96%). 1H NMR (300 MHz, CDCl3) δ7.22 (s, 4H), 4.15 (q, J=6 Hz, 2H), 3.57 (s, 2H), 2.47 (s, 3H), 1.25 (t, J=6 Hz, 3H).

Workup

  1. concentrationconcentrated at reduced pressure
  2. customThe residue was partitioned between methylene chloride and sodium bicarbonate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d7f03197ea624094b1b055e39d18aa5a
Source dataset
uspto-grants-2002_07
Patent number
US06420349B1

Reaction notes

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