Methanol → Methyl 3-fluoro-4-hydroxybenzoate

HRID 404370

反応式

HRID 404370 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH3:17])=[O:6]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1604563-Fluoro-4-hydroxybenzoic acid

生成物 1

HCID 7019368Methyl 3-fluoro-4-hydroxybenzoate収率 87%

反応条件

温度
80 °C

実験手順

To a round bottom flask containing 3-fluoro-4-hydroxybenzoic acid (5.03 g, 32.22 mmol) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) was added a cold solution of MeOH (50.0 mL) and sulfuric acid (2.0 mL). The mixture was heated to 80° C. and monitored with TLC. After 20.5 hours, the solvent was removed and the mixture was diluted with diethyl ether. The organic phase was washed carefully twice with saturated aqueous NaHCO3 and once with brine. The organic phase was then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to afford T33.1 as a white solid (4.79 g, 87% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.81 (2H, m), 7.06 (1H, t, J=8.4 Hz), 5.62 (1H, d, J=4.3 Hz), 3.91 (3H, s).

後処理

  1. customthe solvent was removed
  2. additionthe mixture was diluted with diethyl ether
  3. washThe organic phase was washed carefully twice with saturated aqueous NaHCO3 and once with brine
  4. dry with materialThe organic phase was then dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe organic solvent was removed in vacuo

出典と根拠

ORDレコード
ord-ded54ae526c64e18818ef33c952d007a
出典データセット
uspto-grants-2014_06
特許番号
US08748462B2

関連ノート

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