Water → HCID 67543117, compound

HRID 2061018Notes

Reaction equation

HRID 2061018 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].[OH-].[Na+].O>C(O)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

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59498152HCID 59498152, compound

Product 1

HCID 67543117HCID 67543117, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.39 g (19.8 mmol) of (E)-methyl 2-ethyl-3-(phenylthio)-2-propenoate and 20 ml of an aqueous 2N NaOH solution in 40 ml of ethanol was stirred at 80° C. for 2 hours and then cooled to room temperature. To the reaction mixture was added 100 ml of water and washed with t-butyl methyl ether. The aqueous layer was acidified to pH 2 with concentrated HCl and extracted with tert-butyl methyl ether. The organic layer was washed with a saturated NaCl solution, dried over anhydrous MgSO4, and concentrated to obtain 4.07 g of 2-ethyl-3-(phenylthio)-2-propenoic acid.

Workup

  1. washwashed with t-butyl methyl ether
  2. extractionextracted with tert-butyl methyl ether
  3. washThe organic layer was washed with a saturated NaCl solution
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fc976faf55334274832c247a7c7c2f97
Source dataset
uspto-grants-2012_10
Patent number
US08278473B2

Reaction notes

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