Ethanol → 3-(4-Tert-butylphenyl)propanoic acid

Participants

Reaction Steps

A 3 L autoclave was charged with wet t-butylcinnamic acid (248 g, 1.21 mol), tetrahydrofuran (1 L), and ethanol (1 L) and palladium on carbon (35 g). The reactor was shut and 90 psi of hydrogen pressure applied and the reactor held at room temperature overnight. The reaction was then transferred to a round bottom flask and concentrated to 200 mL. The formed crystals were decanted and washed with hexane to give 3-(4-t-butylphenyl)propionic acid (52.9 g after vacuum drying). A second crop from the filtrate yielded additional 3-(4-t-butylphenyl)propionic acid (65.8 g). 1HNMR (CD2Cl2, 500 MHz) δ9.85 (br s, 1H); 7.32 (d, J=8 Hz, 2H); 7.15 (d, JAB=8.5 Hz); 2.91 (t, J=8 Hz, 2H); 2.67 (t, J=8 Hz, 2H); 1.27 (s, 9H).

Provenance & Evidence