Sulfuric Acid → HCID 10965347, compound

Temperature

-20 °C

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.

1. customGrignard reaction procedure
2. customThe organic layer is separated
3. concentrationconcentrated under reduced pressure
4. dissolutionThis residue is dissolved in tetrahydrofuran (60 mL)
5. stirringThe reaction mixture is stirred overnight at room temperature
6. extractionIt is then extracted with ethyl acetate (50 mL)
7. customThe organic layer is dried
8. concentrationconcentrated under reduced pressure
9. customThe residue is recrystallized from ethyl acetate

ORD record

ord-305b804ad43a4942a0ba16777e2ac065

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809539B2