Sodium Hydroxide → HCID 18472452, compound

HRID 566067Notes

Reaction equation

HRID 566067 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][C:13](/[CH:15]=[CH:16]/[C:17]([O:19]C)=[O:18])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.C(O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:14][C:13](/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86756175HCID 86756175, compound

Product 1

HCID 18472452HCID 18472452, compoundYield 89,685.898%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of methyl (E)-3-[5-(4-isopropylphenyl)thiophen-2-yl]acrylate (0.75 mg) in THF/ethanol (10/10 ml) was added at room temperature 2N sodium hydroxide solution (2.0 ml), and the mixture was stirred for 20 hours. Under reduced pressure, the mixture was concentrated, and to the residue was added 1N hydrochloric acid (10 ml). The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated. The resulting crystals were collected by filtration to give pale yellow crystals of (E)-3-[5-(4-isopropylphenyl)thiophen-2-yl]acrylic acid (639.7 mg).

Workup

  1. concentrationUnder reduced pressure, the mixture was concentrated
  2. additionto the residue was added 1N hydrochloric acid (10 ml)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated
  7. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-75728060378344c0924056883030aed0
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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