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

온도

47.5 °C

A solution of (E)-3-cyclooctyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid methyl ester (2.82 g, 8.05 mmol) in ethanol (30 mL) was treated with a 1N aqueous sodium hydroxide solution (20 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 (100 mL) and extracted with diethyl ether (1×75 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 (2×100 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×150 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford (E)-3-cyclooctyl-2-(4-(methanesulfonyl)-phenyl)-acrylic acid (2.64 g, 97%) as a light yellow solid: EI-HRMS m/e calcd for C18H24O4S (M+) 336.1395, found 336.1390.

1. concentrationThe reaction mixture was concentrated in vacuo
2. customto remove ethanol
3. additionThe residue was diluted with water (100 mL)
4. extractionextracted with diethyl ether (1×75 mL)
5. customto remove any neutral impurities
6. extractionthe resulting acid was extracted into ethyl acetate (2×100 mL)
7. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×150 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD 기록

ord-c8f76719d55e46e59ad990fe8051c24e

출처 데이터셋

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06353111B1