Preparation | The methanol (30mL) suspension of stirred 4-hydroxycyclohexane-1-carboxylic acid (SM-1)(15g,104.1mmol) was dropwise added with sulfuric acid (0.9mL,15.6mmol) at room temperature in a nitrogen atmosphere and stirred at RT for 5 hours. After feedstock consumption (TLC monitoring), the reaction was quenched with water (50mL) and extracted with EtOAc (2x 100mL). The combined organic layer was washed with saturated NaHCO3 solution and saline solution. The organic layer is dried and concentrated under reduced pressure on Na2SO4 to provide methyl 4-hydroxycyclohexanarate (13.5g,82%), which is a liquid. |