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

HRID 2208919ノート

反応式

HRID 2208919 の反応式
[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]

参加物

4

反応物 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 23009717HCID 23009717、化合物

生成物 1

HCID 23009748Methyl 5-hydroxy-2-methyl-3-nitrobenzoate収率 80%

実験手順

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 reaction mixture was heated at reflux for 3 h. On completion, the solvent was removed under reduced pressure. Aqueous sodium bicarbonate was added, followed by extraction 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%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h
  3. customOn completion, the solvent was removed under reduced pressure
  4. additionAqueous sodium bicarbonate was added
  5. extractionfollowed by extraction 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

出典と根拠

ORDレコード
ord-5bbb6da1ef2944d6b56a8a93ac378f12
出典データセット
uspto-grants-2016_06
特許番号
US09376422B2

反応ノート

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