Sodium Hydroxide → 3-Methyl-5-nitrobenzoic acid

Temperature

80 °C

A solution of 89A (0.36 g, 1.8 mmol) and aqueous sodium hydroxide (1N, 3 mL, 3 mmol) in a mixture of methanol (1.5 mL) and tetrahydrofuran (3 mL) was heated at 80° C. for 1 h and at rt for 2 h. An additional portion of sodium hydroxide solution (1 mL) was added and the mixture was heated at 80° C. for 5 min. The reaction mixture was concentrated in vacuo, diluted with ethyl acetate and acidified with hydrochloric acid (1N). The aqueous layer was extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated in vacuo to give 89B (0.314 g, 94%) as a white solid. LCMS: 182 (M+1)

1. temperaturethe mixture was heated at 80° C. for 5 min
2. concentrationThe reaction mixture was concentrated in vacuo
3. additiondiluted with ethyl acetate
4. extractionThe aqueous layer was extracted with ethyl acetate (2×)
5. washThe combined organic layers were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD record

ord-ff1deb6e9d1b4c8081f805a8d9b881ba

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222453B2