Methanol → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

HRID 356741ノート

反応式

HRID 356741 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5](=[CH:9][CH:10]=1)[C:6]([O:8][CH3:17])=[O:7]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 57882-Hydroxy-p-toluic acid

生成物 1

HCID 78400Benzoic acid, 2-hydroxy-4-methyl-, methyl ester収率 90%

実験手順

4-Methylsalicylic acid (100 g, 658 mmoles) was dissolved in anhydrous methanol (500 mL) and concentrated sulfuric acid (25 mL) was added carefully. The solution was refluxed for 18 hours, then cooled to room temperature. The reaction mixture was concentrated to about 150 mL, and ethyl acetate (250 mL) was added. The ethyl acetate solution was washed twice with saturated aqueous sodium bicarbonate (250 mL portions) and then with saturated aqueous sodium chloride (100 mL). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered, and evaporated to a clear, reddish-brown liquid. This crude product was vacuum distilled (oil pump) to afford a clear, viscous liquid that solidified on standing to afford 98.1 g (90% yield) of methyl 4-methylsalicylate.

後処理

  1. temperatureThe solution was refluxed for 18 hours
  2. concentrationThe reaction mixture was concentrated to about 150 mL, and ethyl acetate (250 mL)
  3. additionwas added
  4. washThe ethyl acetate solution was washed twice with saturated aqueous sodium bicarbonate (250 mL portions)
  5. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated to a clear, reddish-brown liquid
  8. distillationdistilled (oil pump)
  9. customto afford a clear, viscous liquid that solidified

出典と根拠

ORDレコード
ord-a8dc5e8b7a0d4afeb03740b0c86d7cf0
出典データセット
uspto-grants-1998_11
特許番号
US05837878

反応ノート

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