Sulfuric Acid → 1-[Bis(4-fluorophenyl)methoxy]-4-chlorobutane

HRID 130584

Reaktionsgleichung

Reaktionsgleichung von HRID 130584
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].S(=O)(=O)(O)O.[F:12][C:13]1[CH:27]=[CH:26][C:16]([CH:17](O)[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[F:12][C:13]1[CH:14]=[CH:15][C:16]([CH:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:26][CH:27]=1

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 135694-Chloro-1-butanolHCID 1230494,4'-Difluorobenzhydryl alcohol

Produkt 1

HCID 107573721-[Bis(4-fluorophenyl)methoxy]-4-chlorobutaneAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-chloro-1-butanol (6.51 g, 60 mmol), 1 mL of concentrated sulfuric acid and 4,4′-difluorobenzhydrol (2.2 g, 10 mmol) in 50 mL of toluene was heated at reflux for 12 h. The reaction mixture was cooled, washed successively with saturated sodium bicarbonate solution (50 mL) and water (50 mL). The organic layer was dried over MgSO4, filtered and the solvent was removed by rotary evaporation. The resultant brown oil was purified on a silica gel column. Elution with 2% ethyl acetate/hexane afforded 2.33 g (7.5 mmol, 75%) of the product as a colorless oil. 1H NMR (CDCl3): δ 1.71-1.80 (2H, m), 1.84-1.93 (2H, m), 3.43 (2H, t, J=6.0), 3.52 (2H, t, J=6.4), 5.30 (1H, s) 6.95-7.02 (4H, m), 7.24-7.29 (4H, m)

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 12 h
  3. temperatureThe reaction mixture was cooled
  4. washwashed successively with saturated sodium bicarbonate solution (50 mL) and water (50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed by rotary evaporation
  8. customThe resultant brown oil was purified on a silica gel column
  9. washElution with 2% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-64f9e306bc9c4b59869d343feb79a3a6
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381822B2

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