Iodine → (E)-3-(4-Methoxybenzenesulfonyl)-2-propylacrylic acid

Sodium 4-methoxyphenylsulfinate (10.0 g, 51.49 mmol) was dissolved in water (50 ml). This solution was shaken with iodine (8.7 g, 34.29 mmol) in dichloromethane (60 ml). The dichloromethane layer turned from deep pink to orange. The dichloromethane layer was dried over magnesium sulfate and filtered into a flask containing 2-propylacrylic acid (2.0 g, 17.52 mmol). The solution was stirred overnight at room temperature and then cooled to 0° C. Triethylamine (7.3 ml, 51.49 mmol) was added and the solution was allowed to warm to room temperature over 2 hours. Sulphuric acid (2M, 50 ml) was added to quench the reaction. The organic phase was washed with 10% aqueous sodium bisulphite (50 ml), then extracted with sodium hydroxide (1 g) in water (50 ml). The aqueous layer was washed with MTBE (20 ml) and the acidifed with sulphuric acid (2M, 10 ml). The product was extracted into dichloromethane (2×30 ml) and the combined organic layers were washed with brine (20 ml), dried over magnesium sulfate, filtered and evaporated to give the title compound in 90% yield. This yellow solid was recrystallised from hot solvent (ethyl acetate:heptane:glacial acetic acid 1:1:0.2) to give the title compound as white crystals (4.02 g, 80%).

1. dry with materialThe dichloromethane layer was dried over magnesium sulfate
2. filtrationfiltered into a flask
3. temperaturecooled to 0° C
4. temperatureto warm to room temperature over 2 hours
5. customto quench
6. customthe reaction
7. washThe organic phase was washed with 10% aqueous sodium bisulphite (50 ml)
8. extractionextracted with sodium hydroxide (1 g) in water (50 ml)
9. washThe aqueous layer was washed with MTBE (20 ml)
10. extractionThe product was extracted into dichloromethane (2×30 ml)
11. washthe combined organic layers were washed with brine (20 ml)
12. dry with materialdried over magnesium sulfate
13. filtrationfiltered
14. customevaporated

ORD-Eintrag

ord-f3775748938e4e87b2a4085ffe5b3d4e

Quelldatensatz

uspto-grants-2001_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06274758B1