Sodium Carbonate → 2-[(4-Butoxybenzenesulfonyl)methyl]-2-propenoic acid

HRID 1457351Notes

Reaction equation

HRID 1457351 reaction equation
Br[CH2:2][C:3](=[CH2:7])[C:4]([OH:6])=[O:5].[CH2:8]([O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([OH:21])=[O:20])=[CH:15][CH:14]=1)[CH2:9][CH2:10][CH3:11].[Na].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH2:8]([O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH2:2][C:3](=[CH2:7])[C:4]([OH:6])=[O:5])(=[O:21])=[O:20])=[CH:15][CH:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 5588842-(Bromomethyl)propenoic acidHCID 5360545SodiumHCID 218805424-Butoxybenzenesulfinic acid

Product 1

HCID 219970372-[(4-Butoxybenzenesulfonyl)methyl]-2-propenoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromomethylacrylic acid (1.0 g, 6.0 mmol), 4-butoxybenzenesulfinic acid, sodium salt (3.1 g, 13 mmol), sodium carbonate (1.9 g, 18 mmol) and dimethylformamide (20 mL) is refluxed overnight. The reaction mixture is then partitioned between ethyl acetate and aqueous 10% hydrochloric acid and the organic phase is concentrated in vacuo. The concentrate is chromatographed over silica gel 60 (230-400 mesh) with chloroform/methyl alcohol/acetic acid (94/5/1) and the eluate concentrated in vacuo to afford the title compound as a white solid.

Workup

  1. temperatureis refluxed overnight
  2. customThe reaction mixture is then partitioned between ethyl acetate and aqueous 10% hydrochloric acid
  3. concentrationthe organic phase is concentrated in vacuo
  4. customThe concentrate is chromatographed over silica gel 60 (230-400 mesh) with chloroform/methyl alcohol/acetic acid (94/5/1)
  5. concentrationthe eluate concentrated in vacuo

Sources & evidence

ORD record
ord-b049429386754f0782f67bf0835c0dff
Source dataset
uspto-grants-1998_12
Patent number
US05847153

Reaction notes

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