Lithium Hydroxide → (2E)-3-[4-(Methylsulfonyl)phenyl]propenoic acid

HRID 2212031Notes

Reaction equation

HRID 2212031 reaction equation
C([O:3][C:4](=[O:17])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1)C.[OH-].[Li+]>O1CCOCC1.O>[CH3:16][S:13]([C:10]1[CH:11]=[CH:12][C:7](/[CH:6]=[CH:5]/[C:4]([OH:17])=[O:3])=[CH:8][CH:9]=1)(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10634688HCID 10634688, compound

Product 1

HCID 5702855(2E)-3-[4-(Methylsulfonyl)phenyl]propenoic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of (E)-3-(4-(methylsulfonyl)phenyl)acrylic acid ethyl ester and lithium hydroxide in dioxane/water (100 ml/100 ml) was stirred for 16 h at room temp. It was washed with tert.-butyl methyl ether (200 ml). The aqueous phase was acidified with a 10% aqueous solution of sodium hydrogensulfate until pH 2. The precipitation was isolated by filtration and dried in vacuo. The residue was suspended in ethanol (100 ml). The solvent was removed. The latter procedure was repeated once to give 2.74 g of crude (E)-4-methylsulfonylcinnamic acid which was used in the next step without further purification.

Workup

  1. washIt was washed with tert.-butyl methyl ether (200 ml)
  2. customThe precipitation
  3. customwas isolated by filtration
  4. customdried in vacuo
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-c2645ec8cac940c7bc5fe40dcdf5aa16
Source dataset
uspto-grants-2006_09
Patent number
US07101898B2

Reaction notes

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