Methanol → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

To 4-hydroxymethylcyclohexanecarboxylic acid (TCI-JP, 0.50 g, 3.2 mmol) in 10 mL CH3OH was added 0.50 mL concentrated H2SO4. This mixture was warmed to reflux and allowed to stir for 2 h. The reaction mixture was then cooled and NH4OH was added until the solution tested basic using pH paper. The mixture was then extracted with 3×5 mL ethyl acetate. The combined organic extracts were washed with saturated, aqueous NaCl then were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give 0.45 g of the title compound (0.26 mmol, 83% yield). MS (DCI/NH3) m/z 190 (M+NH4)+.

1. temperatureThis mixture was warmed
2. temperatureto reflux
3. temperatureThe reaction mixture was then cooled
4. extractionThe mixture was then extracted with 3×5 mL ethyl acetate
5. washThe combined organic extracts were washed with saturated, aqueous NaCl
6. dry with materialthen were dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-3725bd42750144efbba18ff6e47dddf1

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560481B2