Ethanol → HCID 67543117, compound

HRID 1882344Notes

Reaction equation

HRID 1882344 reaction equation
[CH2:1]([C:3](=[CH:8][S:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([O:6]C)=[O:5])[CH3:2].C(O)C.[OH-].[Na+].O>COC(C)(C)C>[CH2:1]([C:3](=[CH:8][S:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]([OH:6])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67544987HCID 67544987, compound

Product 1

HCID 67543117HCID 67543117, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

To methyl 2-ethyl-3-(phenylthio)acrylate (4.39 g) were added ethanol (40 mL) and then a 2N aqueous sodium hydroxide solution (20 mL), and the mixture was refluxed at room temperature for 2 hours. After the reaction mixture was cooled to room temperature, water (100 mL) was added thereto, and further tert-butyl methyl ether was added, thereby layers were separated. The aqueous layer was adjusted to pH 2 by addition of conc. hydrochloric acid, and then extracted with tert-butyl methyl ether. The organic layer was washed with a saturated aqueous sodium chloride solution, dried, and then concentrated to obtain 2-ethyl-3-(phenylthio)acrylic acid (4.07 g).

Workup

  1. customlayers were separated
  2. additionThe aqueous layer was adjusted to pH 2 by addition of conc. hydrochloric acid
  3. extractionextracted with tert-butyl methyl ether
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1bc9f2f185674502aa4661a24f233698
Source dataset
uspto-grants-2012_11
Patent number
US08318981B2

Reaction notes

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