Ethanol → 2-(3-Propan-2-ylphenyl)propanoic acid

Participants

Reaction Steps

A mixture of 2-[3′-(isopropenyl)phenyl]ethyl propionate, obtained by the method reported above (1 g; 4.6 mmol), 95% ethyl alcohol (10 ml) and Pd/C 10% (100 mg) are subjected to catalytic hydrogenation at r.t. and atmospheric pressure until the initial reagent disappears (2 h). The catalyst is filtered off on Celite and, after evaporation of the filtrate, a transparent oil is obtained (0.99 g; 4.5 mmol) that is hydrolysed in a 1N solution of KOH in ethyl alcohol (10 ml) at T=80° C. for 2 h. After cooling at r.t. the solvents are evaporates at reduced pressure; the residue is taken up with EtOAc (20 ml) and it is extracted with H2O (3×10 ml); the aqueous phase is acidified to pH=2 with 2N HCl and counter-extracted with EtOAc (2×10 ml); the organic extracts are combined and washed with a saturated solution of NaCl, are dried over Na2SO4 and evaporated at reduced pressure to give 2-[(3′-isopropyl)phenyl]propionic acid (0.75 g; 3.6 mmol)

Provenance & Evidence