Sodium Hydroxide → 4-(Isobutylsulfonyl)benzoic acid

HRID 72993노트

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HRID 72993 반응식
[CH2:1]([S:5]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>O1CCOCC1>[CH2:1]([S:5]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=1)(=[O:7])=[O:6])[CH:2]([CH3:4])[CH3:3]

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 58550723HCID 58550723, 화합물

생성물 1

HCID 247087824-(Isobutylsulfonyl)benzoic acid수율 105.8%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-19a7897f8c884c2aacc01502d907d89e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828996B2

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