Isopropanol → 5-Cyano-2-isopropoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

To 198 mmol isopropanol was added 19.8 mmol sodium and the mixture was then heated at 100° C. until all the sodium was dissolved (30 min.). Susbsequently, 6.59 mmol 5-cyano-2-iodobenzoic acid [CAS: 219841-92-6; WO9901455] and 1.32 mmol copper (I) bromide were added and the reaction mixture heated at 120° C. for 2 h. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The residue was suspended in 50 ml 1 M aq HCl and extracted 3× with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. Flash chromatography on silica gel (eluant: heptane/ethyl acetate) provided the title compound as a white solid (yield 55%). MS (m/e): 204.1 ([M−H]−, 100%).

Provenance & Evidence