4-Toluenesulfonyl chloride → HCID 13463456, compound

Reaction equation

[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][CH:13]([CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[CH3:12][C@@H:13]([CH2:20][CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)(=[O:9])=[O:8]

Participants

Procedure

A solution of p-toluenesulfonyl chloride (19.9 g, 0.1 mol) dissolved in toluene (30 ml) was dropwise added with stirring under ice cooling, to a solution of 6-methyloctanol (15.4 g, 0.1 mol) prepared according to the method of a literature (M.C.L.C. 27,417 (1974)) and dissolved in dry pyridine (43 ml), followed by slowly returning the temperature to room temperature, allowing the resulting material to stand overnight, extracting the reaction mixture with toluene after completion of the reaction, washing the resulting organic layer with 6N-hydrochloric acid, then with 2N-NaOH aqueous solution, further with water until the washing water became neutral, drying the layer, and distilling off toluene to obtain oily (S)-6-methyloctyl-p-toluenesulfonate (26.1 g).