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

Temperature

20 °C

To a solution of 6-phenylsulfanyl-hexa-2,4-dienoic acid methyl ester (0.34 g, 1.45 mmol) in methanol (5 mL) were added aqueous sodium hydroxide (1M, 5 mL, 5 mmol) and distilled water (20 mL). The stirred mixture was heated at reflux for 1 hour, allowed to cool to 20° C., and then concentrated under reduced pressure to about 10 mL. 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, 10 mL) at 0° C. The mixture was shaken, the organic layer was separated and washed successively with saturated aqueous sodium hydrogen carbonate (25 mL), distilled water (25 mL), and brine (25 mL), then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a pale yellow solid that was recrystallised from diethyl ether/hexanes to give the title compound (0.30 g, 93%) as a white solid, mp 108-110° C.

1. distillationdistilled water (20 mL)
2. temperatureThe stirred mixture was heated
3. temperatureat reflux for 1 hour
4. concentrationconcentrated under reduced pressure to about 10 mL
5. washThe aqueous solution was washed with diethyl ether (50 mL)
6. additionpoured onto a mixture of ethyl acetate (50 mL) and hydrochloric acid (2M, 10 mL) at 0° C
7. customthe organic layer was separated
8. washwashed successively with saturated aqueous sodium hydrogen carbonate (25 mL)
9. distillationdistilled water (25 mL), and brine (25 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 diethyl ether/hexanes

ORD record

ord-22a8de56e3bd417caecc5e7969bc95b3

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2