Sodium Hydroxide → (E)-3-[4-(4-methylphenyl)thiophen-2-yl]acrylic acid

HRID 1387952Notes

Reaction equation

HRID 1387952 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10](/[CH:13]=[CH:14]/[C:15]([O:17]C)=[O:16])[S:11][CH:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10](/[CH:13]=[CH:14]/[C:15]([OH:17])=[O:16])[S:11][CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86756171methyl (E)-3-[4-(4-methylphenyl)thiophen-2-yl)acrylate

Product 1

HCID 11253577(E)-3-[4-(4-methylphenyl)thiophen-2-yl]acrylic acidYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (E)-3-[4-(4-methylphenyl)thiophen-2-yl)acrylate (2.40 g) in tetrahydrofuran (50 ml) was added 2N sodium hydroxide (6.0 ml) at room temperature, and the mixture was stirred for 6 days. Precipitated crystal was collected by filtration and washed with tetrahydrofuran. To the crystals was added 1N hydrochloric acid (20 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure to give (E)-3-[4-(4-methylphenyl)thiophen-2-yl]acrylic acid (1.24 g) as pale yellow crystals.

Workup

  1. customPrecipitated crystal
  2. filtrationwas collected by filtration
  3. washwashed with tetrahydrofuran
  4. additionTo the crystals was added 1N hydrochloric acid (20 ml)
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-712148fdcc5a4ee595d3c488f3a21c53
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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