Water → 3-Methylthio-4-chromanone

Participants

Reaction Steps

The sulfonium salt compound expressed by structural formula [6] was synthesized as follows. First, the present inventor prepared 3-bromo-4-chromanone. The 3-bromo-4-chromanone was synthesized in accordance with the report by W. S. Johnson et. al. in J. Am. Chem. Soc., vol. 66, pages 218-220, 1944. 10.4 grams of 3-bromo-4-chromanone was dissolved in 42 milli-litters of ethanol. 21.3 milli-litters of 15% water solution of methyl-mercaptan sodium salt was dropped thereinto. The resultant solution was agitated at room temperature for 2 hours, and the resultant mixture was poured into cold water. An organic layer was extracted by using 200 milli-litters of ether, and the ether layer was washed in sodium chloride and, thereafter, water. The ether layer was dried by using magnesium sulfate, and the solvent was removed in low pressure. The residue was put in a silica gel column. Using eluate containing hexane and ethyl acetate at 3:1, the residue was separated and refined. Then, 1.52 grams of 3-methylthio-4-chromanone was obtained. The yield was 17%.

Provenance & Evidence