Hydrochloric Acid → 2-Chloro-4-ethenylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

To solution of 2-chloro-4-vinyl-benzoic acid methyl ester (50 mg, 0.26 mmol) in THF (2 ml) was added 2M NaOH (1 ml). The solution was heated to 70° C. for 1 hour. The reaction was cooled back to room temperature and brought to a pH of ˜3 with 1M HCl. The aqueous solution was extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated down under reduced pressure to give 2-chloro-4-vinyl benzoic acid as a white solid. Amount obtained: 40.3 mg (86%). LCMS (M/Z): 183 (M+H); 1H NMR (Chloroform-d) δ: 5.47 (d, J=10.9 Hz, 1 H) 5.93 (s, 1 H) 6.70 (dd, J=17.6, 10.9 Hz, 1 H) 7.38 (dd, J=8.2, 1.8 Hz, 1 H) 7.52 (s, 1 H) 8.02 (d, J=8.0 Hz, 1 H).

Provenance & Evidence