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

HRID 1978225Notes

Reaction equation

HRID 1978225 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-780d911a7553446482d1768688718786
Source dataset
uspto-grants-2001_05
Patent number
US06235928B1

Reaction notes

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