Toluene → HCID 13536741, compound

Participants

Reaction Steps

16 g of 3-mercapto-4-hydroxybenzoic acid (III) was dissolved in a mixture of 300 ml of toluene and 50 ml of acetone. 50 ml of boron trifluoride etherate was added and the mixture was stirred at room temperature for 4 hours. Ice (50 g) was added and the mixture was stirred for a further 1 hour. The organic layer was separated, washed with brine, dried with magnesium sulfate and evaporated to leave a solid residue. The residue was recrystallized from aqueous methanol to yield 15 g of 5-carboxy-2,2-dimethyl-1,3-benzoxathiole (IV), m.p. 124°-125° C.

Provenance & Evidence