Sodium Hydroxide → 4-Cyclopropyl-5-iodo-2-methylbenzoic acid

Temperature

60 °C

Into a 500-mL round-bottom flask, was placed a solution of methyl 4-cyclopropyl-5-iodo-2-methylbenzoate (compound 86.2, 15.0 g, 47.5 mmol) in methanol (150 mL). A solution of sodium hydroxide (5.70 g, 143 mmol) in water (75 mL) was added and the resulting solution was stirred for 4 h at 60° C., then cooled to room temperature. The volatiles were removed under reduced pressure and the remaining solution was adjusted to pH 3 with aqueous hydrogen chloride (12 M). The mixture was extracted with ethyl acetate (2×200 mL) and the combined organic extracts were washed with NH4Cl (aq.) (2×400 mL) and brine (400 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 13.0 g (91%) of the title compound as a light yellow solid.

1. customInto a 500-mL round-bottom flask, was placed
2. temperaturecooled to room temperature
3. customThe volatiles were removed under reduced pressure
4. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
5. washthe combined organic extracts were washed with NH4Cl (aq.) (2×400 mL) and brine (400 mL)
6. dry with materialThe organic layer was dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-d121bee1bdf940149134619f74b87695

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2