Sulfuric Acid → 4-(3-Fluorophenoxy)butanoic acid

HRID 440681

반응식

HRID 440681 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][CH2:7][CH2:8]O.[Cr](O)(O)(=O)=O.S(=O)(=O)(O)[OH:19].[CH:23]([OH:26])(C)C>O>[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][CH2:7][CH2:8][C:23]([OH:26])=[O:19]

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 24425Chromic AcidHCID 150860143-(3-Fluorophenoxy)propan-1-OL

생성물 1

HCID 64860154-(3-Fluorophenoxy)butanoic acid

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a stirred solution of 12.0 grams (0.071 mole) of 3-(3-fluorophenoxy)propanol in 150 mL of acetone Jones reagent (a mixture of chromic acid and sulfuric acid in water) was added dropwise until an orange color persisted in the reaction mixture. Isopropanol was then added dropwise until the color of the reaction mixture became blue/green. The reaction mixture was then slurried with silica gel and filtered. The filter cake was washed with ethyl acetate. The combined wash and filtrate were concentrated under reduced pressure to a residue, which was dissolved in methylene chloride and washed with water. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 12.8 grams of 3-(3-fluorophenoxy)propanecarboxylic acid. The NMR spectrum was consistent with the proposed structure.

후처리

  1. additionwas added dropwise until an orange color
  2. filtrationfiltered
  3. washThe filter cake was washed with ethyl acetate
  4. washThe combined wash
  5. concentrationfiltrate were concentrated under reduced pressure to a residue, which
  6. dissolutionwas dissolved in methylene chloride
  7. washwashed with water
  8. dry with materialThe organic layer was dried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1d88b1f766a74de98f47b944c459dede
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521147

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