Hydrochloric Acid → (4-Ethoxymethylsulfanyl-phenyl)-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A 100 mL 3-necked round bottom flask is charged with (4-mercapto-phenyl)-acetic acid ethyl ester (10 g, 0.0151 mol), followed by the addition of (20 mL) acetonitrile. The reaction mixture is cooled to 0° C. followed by the addition of 10 mL (0.13 mol) of pyridine and 5.30 g (0.056 mol) of chloromethylethyl ether in 10 mL of acetonitrile in a dropwise manner. The reaction mixture is brought to RT followed by heating at reflux for 24 h. The reaction is worked up by evaporating the solvent under vacuum. The residue thus obtained is diluted with water (20 mL) followed by addition of di lute aqueous hydrochloride solution. This is extracted with ethyl acetate (2×100 mL). The organic layer is washed with dilute aqueous hydrochloric acid solution, water and finally with brine. The organic layer is dried over sodium sulfate and evaporated under vacuum to give (4-ethoxymethylsulfanyl-phenyl)-acetic acid ethyl ester as yellow oil.

Provenance & Evidence