Hydrochloric Acid → HCID 53644717, compound

Participants

Reaction Conditions

Reaction Steps

2 g (0.00665 mol) of S-methyl 2-(2,5-dimethylphenoxymethyl)-phenylthioacetate and 2 g (0.0115 mol) of bis-(dimethylamino)-tert-butoxymethane are heated to 60° C. for 1 hour. The mixture is then admixed with 6 ml of dimethylformamide and 3 ml of concentrated aqueous hydrochloric acid and heated to 60° C. for a further hour. The reaction mixture is admixed with water and extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. The resulting crude intermediate, S-methyl 2-[2-(2,5-dimethylphenoxymethyl)-phenyl]-2-hydroxymethylidene-thio acetate, is dissolved in 10 ml of dimethylformamide, admixed first with 1.6 g (0.0116 mol) of potassium carbonate and then with 0.8 g (0.00634 mol) of dimethyl sulphate and stirred at 20° C. for 24 hours. The mixture is poured into water and extracted with dichloromethane, the organic phase is dried over sodium sulphate, the solvent is distilled off under reduced pressure and the residue is chromatographed over silica gel using diethyl ether/petroleum ether (1:1). 0.5 g (22.9% of theory) of S-methyl 2-[2-(2,5-dimethylphenoxymethyl)-phenyl]-2-methoxymethylidene-thioacetate is obtained.

Provenance & Evidence