2-Chloro-3-nitrobenzoic acid → (2-Chloro-3-nitrophenyl)methanol

Participants

Reaction Conditions

Reaction Steps

3-Nitro-2-chlorobenzoic acid (25.51 g, 126.56 mmol) was dissolved in anhydrous THF (400 mL) under a nitrogen atmosphere. The solution was cooled to −70° C. (internal temperature) under N2 flush. DIBAL-H (260 mL, 1.0M in hexanes) was added dropwise over about 1½ h (internal temperature was maintained below −65° C.). The reaction was allowed to slowly warm to room temperature and was stirred 12 h. The reaction was cooled to −70° C. and 50 mL of MeOH was added dropwise. The reaction mixture was placed in an H2O/ice bath and a 1M Rochelle's salt solution was slowly added in. This solution was stirred for 1 h at room temperature, then filtered through diatomaceous earth. The THF was concentrated in vacuo and the remaining aqueous solution was extracted 3 times with EtOAc. The combined organic layers were washed with brine, dried with MgSO4, filtered, and evaporated to obtain 14.4 g (61%) of the desired 3-nitro-2-chlorobenzyl alcohol as a yellow solid.

Provenance & Evidence