Methane → Methyl 4-(p-toluene-sulphonyl)-butanoate

Participants

Reaction Steps

25 g. Methyl 4-hydroxybutanoate were mixed with 47.5 g. toluene-sulphonyl chloride and 250 ml. dry pyridine at 5° C. and kept at this temperature for 17 hours, whereafter the reaction mixture was poured into 2 liters ice water. The oil thus formed was extracted with diethyl ether and the ethereal extract was washed with 500 ml. 6 N hydrochloric acid to remove excess pyridine, followed by washing with a saturated aqueous solution of sodium bicarbonate until neutral. Concentration of the organic layer gave 32.5 g. of a yellow oil which was dissolved in diethyl ether, treated with decolorising charcoal, filtered and the filtrate concentrated to give 30.5 g. of a pale yellow oil which slowly crystallised at 5° C. Thin layer chromatography (petroleum ether/dichloromethane/acetone 6:3:1 v/v/v) showed the product to be pure. The methyl 4-(p-toluene-sulphonyl)-butanoate thus obtained had a melting point of 23° C.

Provenance & Evidence