Hydrochloric Acid → 7-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

HRID 362843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 362843
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16])=[CH:8][CH:7]=1.Cl>C(=S)=S>[F:5][C:6]1[CH:11]=[C:10]2[C:9]([CH2:12][CH2:13][CH2:14][C:15]2=[O:16])=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 232935944-(4-Fluorophenyl)butyryl chloride

Produkt 1

HCID 103747647-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel2×

Versuchsvorschrift

To a mixture of aluminum chloride (66 g, 0.50 mol) in carbon disulfide (600 mL) was added dropwise a solution of 4-(4-fluorophenyl)butyryl chloride (75.3 g, 0.37 mole) in carbon disulfide (260 mL) keeping the internal temperature below 10° C. After refluxing for 0.5 h, the reaction mixture was poured into a mixture of concentrated HCl (50 mL) and ice water (800 mL). The mixture was filtered and extracted with diethyl ether. The diethyl ether extracts were dried and concentrated it7 vacuo to give crude 7-fluoro-1-tetralone. Vacuum distillation gave pure 7-fluoro-1-tetralone b.p., 83° C. at 0.3 mm Hg which solidified to a white solid (94%). m.p., 62°-64° C. (lit, J. Am. Chem. Soc., 89, 386, 1967, m.p., 63.5°-65.0° C.);

Aufarbeitung

  1. customthe internal temperature below 10° C
  2. temperatureAfter refluxing for 0.5 h
  3. filtrationThe mixture was filtered
  4. extractionextracted with diethyl ether
  5. dry with materialThe diethyl ether extracts were dried
  6. concentrationconcentrated it7 vacuo
  7. customto give crude 7-fluoro-1-tetralone
  8. distillationVacuum distillation

Quellen und Nachweise

ORD-Eintrag
ord-66cebfa730b74ba58f9a1393664ce413
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872118

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