Sodium Hydroxide → HCID 67483058, compound

Temperature

47.5 °C

A solution of (E)-2-(4-(methanesulfonyl)-phenyl)-pentenoic acid methyl ester (1.83 g, 6.82 mmol) in ethanol (30 mL) was treated with a 1N aqueous sodium hydroxide solution (15 mL). The solution was heated at 45-50° C. for 15 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was concentrated in vacuo to remove ethanol. The residue was diluted with water (50 mL) and extracted with diethyl ether (1×50 mL) to remove any neutral impurities. The aqueous layer was then acidified with a 1N aqueous hydrochloric acid solution, and the resulting acid was extracted into ethyl acetate (2×70 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford (E)-2-(4-(methanesulfonyl)-phenyl)-pentenoic acid (1.43 g, 82%) as a black solid: EI-HRMS m/e calcd for C12H14O4S (M+H)+ 254.0621, found 254.0623.

1. concentrationThe reaction mixture was concentrated in vacuo
2. customto remove ethanol
3. additionThe residue was diluted with water (50 mL)
4. extractionextracted with diethyl ether (1×50 mL)
5. customto remove any neutral impurities
6. extractionthe resulting acid was extracted into ethyl acetate (2×70 mL)
7. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×100 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-ce41ec4450984d4eb452ad6978c8a283

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353111B1