Sodium Hydroxide → 6-Benzenesulfinyl-hexa-2,4-dienoic acid

Temperature

20 °C

To a solution of 6-benzenesulfinyl-hexa-2,4-dienoic acid methyl ester (0.243 g, 0.97 mmol) in methanol (2.0 mL) were added a solution of aqueous sodium hydroxide (1M. 4.0 mL, 4 mmol) and distilled water (10 mL). After stirring at reflux for one hour, the mixture was allowed to cool to 20° C. and was concentrated under reduced pressure. The solution was washed with diethyl ether (25 mL) and then poured onto a mixture of ethyl acetate (20 mL) and hydrochloric acid (2M, 5 mL) at 0° C. The mixture was shaken, and the organic layer separated and washed successively with saturated aqueous sodium hydrogen carbonate (10 mL), distilled water (10 mL), brine (10 mL), then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a pale yellow solid that was recrystallised from ether/hexanes to give the title compound (0.204 g, 89%) as a white solid.

1. distillationdistilled water (10 mL)
2. temperatureat reflux for one hour
3. concentrationwas concentrated under reduced pressure
4. washThe solution was washed with diethyl ether (25 mL)
5. additionpoured onto a mixture of ethyl acetate (20 mL) and hydrochloric acid (2M, 5 mL) at 0° C
6. stirringThe mixture was shaken
7. customthe organic layer separated
8. washwashed successively with saturated aqueous sodium hydrogen carbonate (10 mL)
9. distillationdistilled water (10 mL), brine (10 mL)
10. dry with materialdried over anhydrous MgSO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customto give a pale yellow solid
14. customthat was recrystallised from ether/hexanes

ORD record

ord-98e88570898646ac85b972949c91bf59

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2