[Cl-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[H][H].[OH:11][C:12]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:13]=1[CH:14]=[O:15]>O1CCCC1.O>[OH:15][CH:14]1[C:13]2[CH:16]=[CH:17][C:18]([CH3:20])=[CH:19][C:12]=2[O:11][CH2:2]1To a solution of trimethylsulfoxonium chloride (12.9 g) in tetrahydrofuran (200 ml) was added sodium hydride (2.4 g of 100%). This solution was heated at reflux until hydrogen evolution had ceased. 13.6 g of 2-hydroxy-4-methylbenzaldehyde dissolved in tetrahydrofuran (100 ml) was then added. The reaction mixture was refluxed until the reaction was complete (3 hours). It was then poured into water (600 ml), extracted with ether, the ether dried over sodium sulphate and evaporated to give 3-hydroxy-6-methyl-2,3-dihydrobenzofuran.
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