Methanol → Methyl 5-hydroxy-2-nitrobenzoate

HRID 631275

반응식

HRID 631275 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:18]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:18])=[O:8]

참가 물질

4

반응물 3

HCID 887MethanolHCID 118825-Hydroxy-2-nitrobenzoic acidHCID 24386Thionyl Chloride

생성물 1

HCID 12922678Methyl 5-hydroxy-2-nitrobenzoate수율 98%

실험 절차

To MeOH (125 mL) was added 5-hydroxy-2-nitrobenzoic acid (1.02 g, 5.6 mmol) followed by dropwise addition of thionyl chloride (˜4 mL) and the mixture heated at reflux overnight. The solution was cooled to room temperature, concentrated in vacuo, reconcentrated twice from MeOH, dissolved in EtOAc, washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo to give methyl 5-hydroxy-2-nitrobenzoate (1.09 g, 5.5 mmol, 98%). 1H NMR (300 MHz, DMSO-d6) δ 11.38 (s, 1H), 8.05 (d, 1H), 7.03 (d, 1H), 7.01 (s, 1H), 3.82 (s, 3H); LC-MS (ESI) m/z 196 (M−H)+.

후처리

  1. temperaturethe mixture heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. dissolutiondissolved in EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-998760860f08408bb1c98a03bca00e41
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09320739B2

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