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

Temperature

40 °C

A solution of (E)-3-cyclohexyl 2-(3,4-difluoro-phenyl)-acrylic acid methyl ester (0.55 g, 1.97 mmol) in ethanol (10 mL) was treated with a 1N aqueous sodium hydroxide solution (4 mL). The solution was heated at 40° 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 (30 mL) and then acidified with a 1N aqueous hydrochloric acid solution. The resulting acid was extracted into ethyl acetate (2×30 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford (E)-3-cyclohexyl-2-(3,4-difluoro-phenyl)-acrylic acid (0.51 g, 97%) as a white solid: mp 119-121° C.; EI-HRMS m/e calcd for C15H16F2O2 (M+H)+267.1196, found 267.1200.

1. concentrationThe reaction mixture was then concentrated in vacuo
2. customto remove ethanol
3. additionthe residue was diluted with water (30 mL)
4. extractionThe resulting acid was extracted into ethyl acetate (2×30 mL)
5. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-d251a2bb00ec4a0ca4445000138126bd

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06353111B1