Sulfuric Acid → HCID 10965347, compound

Participants

Reaction Conditions

Reaction Steps

A solution of isopropylmagnesium bromide is prepared from isopropyl bromide (41.0 g, 0.33 mol) and magnesium turnings (10.0 g, 0.41 mol) in tetrahydrofuran (150 mL) by using standard Grignard reaction procedure. This solution is added to a solution of 4-formylbenzoic acid (5.0 g, 0.033 mol) in tetrahydrofuran (50 mL) at −20° C. over a period of 30 minutes. It is then stirred at −20° C. for 1 hour and then treated with aqueous ammonium chloride solution (150 mL). The organic layer is separated and concentrated under reduced pressure. This residue is dissolved in tetrahydrofuran (60 mL) and the solution is treated with an aqueous solution (8 mL) of sodium dichromate (1.5 g, 0.006 mol) and concentrated sulfuric acid (2 mL). The reaction mixture is stirred overnight at room temperature. It is then extracted with ethyl acetate (50 mL). The organic layer is dried and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate:n-hexane mixture to give 4-isobutyrylbenzoic acid.

Provenance & Evidence