[I-].C[S+](C)(C)=O.[H-].[Na+].[CH3:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[O:11].O1CCC[CH2:21]1.CS(C)=O>CS(C)=O>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([C:10]2([CH3:21])[CH2:9][O:11]2)[CH:17]=[CH:16][CH:15]=1Trimethyloxosulphonium iodide (100 g, 0.45 mole) was added as a slurry in dimethylsulphoxide (100 ml) to a stirred cooled suspension of sodium hydride (22.6 g of a 50% dispersion of oil, washed free from oil with ether) under nitrogen, keeping the internal temperature at 20° C. by ice-cooling. After stirring at room temperature for 1 hour 3-methoxyacetophenone (45 g, 0.3 mole) was added in a 1:1 mixtures of dry tetrahydrofuran-dimethylsulphoxide (100 ml). The reaction mixture was slowly heated to 50° C. over 1 hour and this temperature was maintained for 1 hour. The mixture was cooled, poured on to ice water and extracted with ether (4×150 ml). The combined extracts were washed with brine, dried (MgSO4) and evaporated to an oil (34.0 g) and used crude for the preparation of (3-methoxy)-α-methyl-α[(methylamino)methyl]benzene methanol.
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