Methanol → Methyl 3,5-dimethyl-4-nitrobenzoate

HRID 1427076노트

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HRID 1427076 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:14])[C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:19]O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:14])[C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([O:7][CH3:19])=[O:6]

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2494133,5-Dimethyl-4-nitrobenzoic acid

생성물 1

HCID 22998442Methyl 3,5-dimethyl-4-nitrobenzoate수율 98.3%

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온도
80 °C

실험 절차

To a solution of 3,5-dimethyl-4-nitro-benzoic acid (10.0 g, 0.0512 mol) in MeOH (150 mL) is added thionyl chloride (10 ml) at 0° C. and the reaction is heated to 80° C. After 16 h, the reaction mixture is cooled to room temperature and solvent is removed under reduced pressure. The residue is diluted with water (50 ml) and basified with saturated NaHCO3 solution to pH 7-8 and extracted with EtOAc (2×120 mL). The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to afford the title compound as a light yellow solid (10.71 g, 98.3%). 1H NMR (400 MHz, DMSO): δ 7.83 (s, 2H), 3.88 (s, 3H), 2.30 (s, 6H).

후처리

  1. temperaturethe reaction mixture is cooled to room temperature
  2. customsolvent is removed under reduced pressure
  3. additionThe residue is diluted with water (50 ml)
  4. extractionextracted with EtOAc (2×120 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is removed under reduced pressure

출처 및 근거

ORD 기록
ord-b18d208ac31b409a8b5284752b85a93a
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933098B2

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