Isopropanol → Methyl 3-chloro-4-isopropoxybenzoate

Participants

Reaction Steps

To a solution of 1.42 g (7.63 mmol) of methyl 3-chloro-4-hydroxybenzoate, 585 μL (7.63 mmol) of 2-propanol, and 3.0 g (11.45 mmol) of triphenylphosphine in 20 mL of THF at 0° C. was added 2.25 mL (11.45 mmol) of diisopropyl azodicarboxylate. The mixture was allowed to warm up to rt and stirred for 16 hr. The solvent was removed. Chromatography on a Biotage 40+M cartridge using 1:19 v/v EtOAc/hexanes as the eluant afforded 1.77 g (100%) of the title compound: 1H NMR δ 1.41 (d, J=6.2, 6H), 4.63-4.70 (m, 1H), 6.93 (d, J=8.7, 1H), 7.89 (dd, J=2.2, 8.6, 1H), 8.05 (d, J=2.0, 1H).

Provenance & Evidence