Methanol → Methyl 3-fluoro-4-hydroxybenzoate

HRID 404370노트

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HRID 404370 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

HCID 7019368Methyl 3-fluoro-4-hydroxybenzoate수율 87%

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ded54ae526c64e18818ef33c952d007a
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748462B2

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