Hydrochloric Acid → 4-Fluorosalicylic acid

HRID 457950

반응식

HRID 457950 반응식
F[C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[OH-:12].[Na+].Cl>CN1CCN(C)C1=O.O>[F:11][C:9]1[CH:10]=[C:2]([OH:12])[C:3](=[CH:7][CH:8]=1)[C:4]([OH:6])=[O:5]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 741022,4-Difluorobenzoic acid

생성물 1

HCID 676614-Fluorosalicylic acid수율 68.1%

시약·촉매·용매 2

HCID 962Water용매HCID 66611,3-Dimethyl-2-imidazolidinone용매

반응 조건

온도
135 °C

실험 절차

A solution of 2,4-difluorobenzoic acid (100 g, 0.63 mol) in 1,3-dimethyl-2-imidazolidinone (1,400 mL, 0.45 M) was treated with sodium hydroxide (88 g, 2.2 mol) and heated to 135° C. After stirring for 4 h, the solution was cooled 0° C., disolved in water (100 mL), and transferred to a 5 L Erlenmeyer flask and carefully treated with aq HCl (2,800 mL, 2 N). After filtering off the crude product, the precipitate was disolved in ethyl acetate, dried over sodium sulfate and decolorizing charcol, and filtered. The solution was concentrated under reduced pressure and recrystallized from ethyl acetate and heptane to give 4-fluorosalicylic acid (2 crops, 67 g, 68%) as off-white needles. mp: 188–189° C.; Rf 0.26 (20% methanol in dichloromethane).

후처리

  1. temperaturethe solution was cooled 0° C.
  2. filtrationAfter filtering off the crude product
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe solution was concentrated under reduced pressure
  6. customrecrystallized from ethyl acetate and heptane

출처 및 근거

ORD 기록
ord-b43b9eeea7ec4070abc3591f782f46ff
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07189749B2

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