Methanol → 3-Cyclohexylacrylic acid

to a solution of 3-Cyclohexyl-acrylic acid ethyl ester (7.00 g, 38.4 mmol) in dioxane (200 mL) was added lithium hydroxide (4.03 g, 96.1 mmol) dissolved-in-water (70 mL). Because LiOH fell out methanol (170 mL) was added to the reaction. After 4 hours at 70° C. ¾ of the solvent was removed in vacuo. 2 N HCl was added until the pH reached 3. The mixture was treated with ammonium chloride (150 mL) saturated solution. The product was extracted with dichloromethane (200 mL×3). The combined organic phases were washed with saturated sodium solution (50 mL) and dried with magnesium sulfate. After filtration the solvent was removed in vacuo. The liquid was left at room temperature for 48 hours for crystallization to occur. The colourless crystalline product (2.01 g, 13.1 mmol) was obtained in 34% yield. 1H NMR (300 MHz, [D6-DMSO]: δ=1.01-1.37 (m, 5H, cyclohexyl-CH2), 1.55-1.79 (m, 5H, cyclohexyl-CH2), 2.06-2.21 (m, 1H, cyclohexyl-CH); 5.69 (dd, J=15.7 Hz and J=1.5 Hz, 1H, C═C—H), 6.76 (dd, J=15.7 Hz and J=6.8 Hz, 1H, C═C—H), 12.01 (broad s, 1H, OH). 13C NMR (75 MHz, [D6-DMSO]: δ=25.1, 25.4, 31.1 (cyclohexyl-CH2), 39.4 (cyclohexyl-CH), 119.5 and 153.4 (C═C) 167.3 (COON). MS: m/z calcd for (C9H14O2) [M+H]+ 155; found 155.

1. additionwas added to the reaction
2. customAfter 4 hours at 70° C. ¾ of the solvent was removed in vacuo
3. addition2 N HCl was added until the pH
4. additionThe mixture was treated with ammonium chloride (150 mL) saturated solution
5. extractionThe product was extracted with dichloromethane (200 mL×3)
6. washThe combined organic phases were washed with saturated sodium solution (50 mL)
7. dry with materialdried with magnesium sulfate
8. filtrationAfter filtration the solvent
9. customwas removed in vacuo

ORD record

ord-9ac410ff474d416d9eeb4749f527229b

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08227516B2