Hydrochloric Acid → 2-Chloro-4-isopropylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

To solution of 2-chloro-4-isopropyl-benzoic acid methyl ester (68 mg, 0.33 mmol) in THF (3 ml) was added 2M NaOH (3 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-isopropyl-benzoic acid as a yellow solid. Amount obtained: 62.7 mg (96%). 1H NMR (Chloroform-d) δ: 1.28 (d, J=6.8 Hz, 6 H) 2.95 (m, J=14.0, 6.9, 6.9 Hz, 1 H) 7.22 (dd, J=8.1, 1.7 Hz, 1 H) 7.36 (d, J=1.6 Hz, 1 H) 7.99 (d, J=8.2 Hz, 1 H).

Provenance & Evidence