Sodium Hydroxide → (E)-3-cyclohexyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid

Temperature

47.5 °C

A solution of (E)-3-cyclohexyl-2-(4-methanesulfonyl-phenyl)-acrylic acid methyl ester (5.7 g, 17.95 mmol) in ethanol (65 mL) was treated with a 1N aqueous sodium hydroxide solution (54 mL). The solution was heated at 45-50° C. for 15 h, at which time, thin layer chromatography analysis of the mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to remove ethanol, and the residue was diluted with water (100 mL) and extracted with diethyl ether (1×150 mL) to remove any neutral impurities. The aqueous layer was acidified with a 1N aqueous hydrochloric acid solution. The resulting acid was extracted into ethyl acetate (2×150 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×250 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford (E)-3-cyclohexyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid (5.18 g, 94%) as a white solid: mp 195-197° C.; EI-HRMS m/e calcd for C16H20O4S (M+H)+309.1160, found 309.1165.

1. concentrationThe reaction mixture was then concentrated in vacuo
2. customto remove ethanol
3. additionthe residue was diluted with water (100 mL)
4. extractionextracted with diethyl ether (1×150 mL)
5. customto remove any neutral impurities
6. extractionThe resulting acid was extracted into ethyl acetate (2×150 mL)
7. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×250 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-c2cd485919334601a071844f147b6064

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353111B1