Methanol → Methyl 5-hydroxy-2-methyl-3-nitrobenzoate

HRID 2208945노트

반응식

HRID 2208945 반응식
[OH:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:19]O>>[OH:1][C:2]1[CH:3]=[C:4]([N+:12]([O-:14])=[O:13])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:19])=[O:8]

참가 물질

4

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 23009717HCID 23009717, 화합물

생성물 1

HCID 23009748Methyl 5-hydroxy-2-methyl-3-nitrobenzoate수율 80%

실험 절차

To a stirred solution of 5-hydroxy-2-methyl-3-nitrobenzoic acid (3.50 g, 17.8 mmol) in methanol (40 mL), was added thionyl chloride (3.9 mL, 53 mmol) at 0° C. The mixture was heated under reflux for 3 hours and concentrated under reduced pressure. Aqueous sodium bicarbonate was added to the residue which was extracted with ethyl acetate. The combined organic layers were washed with water, dried and concentrated under reduced pressure. The crude material was purified by column chromatography to afford the title compound (3.0 g, 80%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. additionAqueous sodium bicarbonate was added to the residue which
  5. extractionwas extracted with ethyl acetate
  6. washThe combined organic layers were washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material was purified by column chromatography

출처 및 근거

ORD 기록
ord-baa371fb034a493ab338803bba5e0607
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376422B2

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