Methanesulfonyl chloride → Methanesulfonic acid 1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)-ethyl ester
Reaction equation
[CH3:1][CH:2]([OH:16])[CH2:3][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:9]=[CH:8][CH2:7][CH:6]=[CH:5]1.[S:17](Cl)([CH3:20])(=[O:19])=[O:18]>N1C=CC=CC=1>[CH3:1][CH:2]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:3][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH2:7][CH:8]=[CH:9]1Participants
4
Procedure
8 g. of α-methyl-1-phenyl-2,5-cyclohexadien-1-ethanol are dissolved in 50 ml. of pyridine and 6.4 g. of mesyl chloride are added dropwise at 0°-5° C. After stirring at room temperature for 2 hours, the mixture is worked-up as follows: The mixture is treated with ice-water and extracted with ether. The ether phase is washed with 3 N aqueous hydrochloric acid, then washed neutral, dried and concentrated. The crude product obtained is chromatographed on 100 g. of silica gel with ether/petroleum ether (1:1). There is obtained an oily product which crystallizes in the cold. After crystallization from methylene chloride/hexane, there is obtained methanesulfonic acid 1-methyl-2-(1-phenyl-2,5-cyclohexadien-1-yl)-ethyl ester having a melting point of 51°-53° C.