2-Propenoic acid, 3-(4-chlorophenyl)- → beta-(p-Chlorophenyl)propionic acid

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Reaction Steps

To a solution of 1.80 g (10 mmol) of 4-chlorocinnamic acid in 50 mL of THF was added Pd/C (1.04 g, 5% w/w) and the solution was stirred under a hydrogen atmosphere until no further H2 take-up was observed (˜1 h). The solution was filtered through Celite and the solvent removed under reduced pressure to yield 1.82 g (9.8 mmol, 98%) of a white solid: mp. 103-105° C.; 1H NMR (DMSO-d6) δ2.51 (t, 2H, β-CH2), 2.79 (t, 2H, α-CH2), 7.28 (dd, 4H, aromatic CH's), 12.12 (s, 1H, COOH); MS (EI, calculated for C9H9ClO2, 184.0291) m/e 184.0288 (M+).

Provenance & Evidence