2-Methylresorcinol → 4-chloro-2-methyl-benzene-1,3-diol

Participants

Reaction Steps

To a solution of 2-methylresorcinol (40 g, 322 mmol) in 750 ml of methanol was added (45.17 g, 0.338 mol) of N-chlorosuccinimide. The mixture was stirred for 6 hours. The solvent was evaporated and the resulting solid was triturated in 500 ml of a 2:1 mixture of hexane and ethyl acetate. The brown crystalline precipitate (succinimide) was filtered off and rinsed with a little extra solvent. The filtrate was concentrated to give the crude product, which was further purified on silica eluting with 4:1 hexanes/ethyl acetate. Appropriate fractions were combined, and evaporated. The product was crystallized from about 1:8 ether/hexanes to afford 33.1 g (65%) of the desired substituted resorcinol 15b. 1H NMR (DMSO-d6) δ: 9.38 (s, 1H), 8.83 (s, 1H), 6.92 (d, J=8.5 Hz, 1H), 6.33 (d, J=8.5 Hz, 1H), 2.00 (s, 3H).

Provenance & Evidence