Methyl chloroacetate → (Naphthalene-1-sulfonyl)-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 3.1 g (0.019 mol) of naphthalene-1-thiol and 2.94 g (0.021 mol, 1.1 eq) of K2CO3 in 100 mL of propan-2-one cooled at 0° C., 3.15 g (0.029 mol, 1.5 eq) of chloro-acetic acid methyl ester were added in one portion. The ice bath was removed and the reaction mixture was stirred an additional 4 hours. The reaction was filtered, the solvent evaporated and the resulting residue was taken up in 100 mL of MeOH. 14.3 g (0.023 mol, 1.2 eq) of oxone (potassium peroxymonosulfate) were added and the reaction mixture was stirred over night at RT. The salts were filtered off, the solvent evaporated and the residue purified by column chromatography on silica gel with heptane/EtOAc (from 4:1 to 1:2) to afford 2.78 g (55%) of (naphthalene-1-sulfonyl)-acetic acid methyl ester as a light yellow oil, MS: 265 (MH+).

Provenance & Evidence