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

Temperature

20 °C

To a solution of the 6-benzenesulfonyl-hexa-2,4-dienoic acid methyl ester (0.70 g, 2.60 mmol) in methanol (8 mL) were added a aqueous sodium hydroxide 1M, 6.0 mL, 6 mmol) and distilled water (20 mL). After stirring at reflux for 1 hour, the mixture was allowed to cool to 20° C. and was concentrated under reduced pressure. The aqueous solution was washed with diethyl ether (50 mL) and then poured onto a mixture of ethyl acetate (50 mL) and hydrochloric acid (2M, 5 mL) at 0° C. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate (20 mL), distilled water (20 mL), and brine (20 mL), then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a pale yellow solid that was recrystallised from ethyl acetate to give the title compound (0.58 g, 87%) as a white solid, mp 148-150° C.

1. distillationdistilled water (20 mL)
2. temperatureat reflux for 1 hour
3. concentrationwas concentrated under reduced pressure
4. washThe aqueous solution was washed with diethyl ether (50 mL)
5. additionpoured onto a mixture of ethyl acetate (50 mL) and hydrochloric acid (2M, 5 mL) at 0° C
6. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate (20 mL)
7. distillationdistilled water (20 mL), and brine (20 mL)
8. dry with materialdried over anhydrous MgSO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customto give a pale yellow solid
12. customthat was recrystallised from ethyl acetate

ORD record

ord-11c81116c5674208b363db34403e4d1a

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2