O[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[C:9]1(C)[C:10]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:12]=[CH:13][CH:14]=1.N1C=CC=C[CH:21]=1.C>C(OCC)C>[C:13]1([CH3:21])[CH:14]=[CH:9][C:10]([S:15]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])(=[O:16])=[O:17])=[CH:11][CH:12]=125 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.
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