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

HRID 341351

반응식

HRID 341351 반응식
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Br[CH2:10][CH2:11][CH2:12][C:13]([O:15]CC)=[O:14].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+].Cl>CC(=O)CC>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 76300Ethyl 4-bromobutyrate

생성물 1

HCID 64860154-(3-Fluorophenoxy)butanoic acid

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

반응 조건

온도
25 °C

실험 절차

A 1 L 3-neck round bottom flask equipped with a magnetic stirrer bar and a reflux condenser was charged with 17.17 g (150 mmol) of 3-fluorophenol, 33.82 g (165 mmol) of ethyl 4-bromobutyrate, 24.88 g, 180 mmol potassium carbonate and 600 mL of 2-butanone. The slurry heated to reflux. After stirring for 21 hr at reflux, the reaction mixture was cooled to 25° C., filtered and concentrated. The residue was taken up in of water and treated with 150 mL of 2N aqueous sodium hydroxide (300 mmol). The reaction mixture was heated to reflux for 30 min and cooled to 25° C. The brown solution was acidified with aqueous 150 ml of 2N hydrochloric acid. The resulting pink solid was isolated by filtration washing with hexanes to yield 25.04 g, mp 53-54° C. Combustion analysis: Found: C, 60.53; H, 5.79%; F, 9.84%; C10H11FO3 requires C, 60.60; H, 5.59%; F, 9.59%; 1H NMR (d6-DMSO): δ 12.1, bs, 1H (COOH); δ 7.20, dd, 1H, (H para to OR); δ 6.7, m, 3H (aryl H's); δ 3.90, t 2H, (CH2 α to O); δ 2.30, t, 2H (CH2 α to COOR); δ 1.87, p, 2H (CH2 β to ArO and COOH).

후처리

  1. customA 1 L 3-neck round bottom flask equipped with a magnetic stirrer bar and a reflux condenser
  2. temperatureThe slurry heated to reflux
  3. temperatureat reflux
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperatureThe reaction mixture was heated
  7. temperatureto reflux for 30 min
  8. temperaturecooled to 25° C
  9. customThe resulting pink solid was isolated by filtration
  10. washwashing with hexanes
  11. customto yield 25.04 g, mp 53-54° C

출처 및 근거

ORD 기록
ord-a034c42d4db94c54b90ff97dc1d4b828
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895777B2

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