Methanol → Methyl 3-fluoro-4-hydroxybenzoate

HRID 404339ノート

反応式

HRID 404339 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 (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (5.03 g, 32.22 mmol) 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 resulting mixture was diluted with diethyl ether. The organic phase was washed carefully two times with saturated aqueous NaHCO3, once with brine, and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to afford T10.1 as a white solid (4.79 g, 87% yield). 1H NMR (400 MHz, CDCl3) 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 resulting mixture was diluted with diethyl ether
  3. washThe organic phase was washed carefully two times with saturated aqueous NaHCO3
  4. dry with materialonce with brine, and 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-337ee80103ea4c7fba08271b9b856f9c
出典データセット
uspto-grants-2014_06
特許番号
US08748462B2

反応ノート

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