Dimethylformamide → Methyl 2-methoxy-3-methylbenzoate

HRID 1443263

反応式

HRID 1443263 の反応式
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].O[C:8]1[C:16](C)=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=O.[CH3:18]I.CN(C)[CH:22]=[O:23]>>[CH3:18][O:2][C:1](=[O:4])[C:16]1[CH:15]=[CH:14][CH:13]=[C:9]([CH3:10])[C:8]=1[O:23][CH3:22]

参加物

5

反応物 4

HCID 6228Dimethylformamide2 回HCID 6328Methyl iodideHCID 67383-Methylsalicylic AcidHCID 11430Potassium Carbonate

生成物 1

HCID 13229229Methyl 2-methoxy-3-methylbenzoate収率 59.3%

実験手順

199.9 g (1.45 mol) of potassium carbonate is introduced into 1.5 l of dimethylformamide. At room temperature, 100 g (657.29 mmol) of 2-hydroxy-3-methylbenzoic acid, dissolved in 250 ml of dimethylformamide, is added in drops. After 30 minutes of stirring, 90 ml of methyl iodide is added in drops, and the batch is stirred overnight. The reaction mixture is added to ice water and extracted three times with methyl tert-butyl ether. The organic phases are washed with water and brine. After drying, the solvent is spun off, and the residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 70.21 g (59.3%) of the desired compound is isolated.

後処理

  1. additionis added in drops
  2. stirringthe batch is stirred overnight
  3. extractionextracted three times with methyl tert-butyl ether
  4. washThe organic phases are washed with water and brine
  5. customAfter drying
  6. customthe residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-1ad544ab0bb2455f8fe4bebceb0c3d8f
出典データセット
uspto-grants-2010_02
特許番号
US07659297B2

関連ノート

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