3-Formyl-4-methylbenzoic acid → 3-(1-Hydroxy-3-buten-1-yl)-4-methylbenzoic acid

Temperature

-5 °C

Into a 100-mL 3-necked round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 3-formyl-4-methylbenzoic acid (compound 4.1, 2.00 g, 12.2 mmol) in tetrahydrofuran (50 mL). The mixture was cooled to −10 to 0° C. then allylmagnesium bromide (1M in Et2O, 24.4 mL, 24.4 mmol) was added drop-wise. The resulting mixture was stirred for 1 hr at −10-0° C., then carefully quenched with saturated aqueous NH4Cl (50 mL) and diluted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous NH4Cl (80 mL) and brine (2×80 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound as a light red solid (2.4 g, crude), which was used in the next step without further purification.

1. customInto a 100-mL 3-necked round-bottom flask, which was purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customcarefully quenched with saturated aqueous NH4Cl (50 mL)
4. additiondiluted with ethyl acetate (200 mL)
5. washThe organic layer was washed with saturated aqueous NH4Cl (80 mL) and brine (2×80 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-57b4d753a52d4121acb42c40ac095142

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2