Methanol → Methyl 5-hydroxy-2-nitrobenzoate

HRID 631275

反応式

HRID 631275 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

HCID 12922678Methyl 5-hydroxy-2-nitrobenzoate収率 98%

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-998760860f08408bb1c98a03bca00e41
出典データセット
uspto-grants-2016_04
特許番号
US09320739B2

関連ノート

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