Sodium Hydroxide → 4-(Isobutylsulfonyl)benzoic acid

Temperature

80 °C

A mixture of methyl 4-isobutylsulfonylbenzoate (1.0 g, 3.9 mmol), NaOH solution (10 mL of 1 M, 10.00 mmol), and dioxane (10 mL) was heated at 80° C. for 1.5 hours. The reaction mixture was cooled to room temperature, then concentrated in vacuo. The solid residue was dissolved in water and washed with ethyl acetate (1×10 mL). The aqueous layer was acidified with 1N HCl solution and was extracted with ethyl acetate (2×10 mL) and layers were separated. The combined organics were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography using (0-100%) ethyl acetate/hexanes as eluent to give 4-isobutylsulfonylbenzoic acid (1.0 g, 98%). ESI-MS m/z calc. 242.1. found 243.2 (M+1)+; Retention time: 1.73 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 8.30 (d, J=8.3 Hz, 2H), 8.05 (d, J=8.3 Hz, 2H), 3.03 (d, J=6.5 Hz, 2H), 2.27 (dt, J=13.3, 6.6 Hz, 1H), 1.08 (d, J=6.7 Hz, 6H).

1. temperatureThe reaction mixture was cooled to room temperature
2. concentrationconcentrated in vacuo
3. dissolutionThe solid residue was dissolved in water
4. washwashed with ethyl acetate (1×10 mL)
5. extractionwas extracted with ethyl acetate (2×10 mL) and layers
6. customwere separated
7. washThe combined organics were washed with brine
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated in vacuo
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-75015b44f8234ed28595f15d2613daa6

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181273B2