3,4-Difluorobenzoyl chloride → HCID 178444574, Verbindung

HRID 2309669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2309669
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[F:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[F:23])[C:17](Cl)=[O:18]>N1C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH2:1]([C@H:6]1[CH2:7][CH2:8][C@H:9]([O:12][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:22]([F:23])=[C:14]([F:13])[CH:15]=2)[CH2:10][CH2:11]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

6

Edukt 2

HCID 27245193,4-Difluorobenzoyl chlorideHCID 178444573HCID 178444573, Verbindung

Produkt 1

HCID 178444574HCID 178444574, VerbindungAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of trans-4-pentylcyclohexanol (1.9 g 0.011 mol) dissolved in dry pyridine (5 ml) was added a solution of 3,4-difluorobenzoyl chloride (2.0 g, 0.011 mol) dissolved in dry toluene (10 ml), followed by heating the mixture at 60° C. for 3 hours, thereafter pouring the reaction mixture in water (100 ml), separating the toluene layer, washing it with 6N hydrochloric acid, then with 2N-NaOH aqueous solution and further with water, drying with anhydrous sodium sulfate, distilling off toluene from the resulting toluene solution and recrystallizing the remaining oily product from ethanol to obtain the objective 3,4-difluorobenzoic acid-trans-4-pentylcyclohexyl ester (2.4 g, 0.0077 mol) (yield: 70%). This product has a m.p. of 26.9° C., and its N-I point sought from a mixture thereof with trans-4-alkyl-(4-cyanophenyl)cyclohexanes according to extrapolation method was -6.0° C. Further its elemental analysis values were as follows: C: 70.03%, H: 7.81% (calculated values, C: 69.65% and H: 7.79%).

Aufarbeitung

  1. customseparating the toluene layer
  2. washwashing it with 6N hydrochloric acid
  3. dry with materialwith 2N-NaOH aqueous solution and further with water, drying with anhydrous sodium sulfate
  4. distillationdistilling off toluene from the resulting toluene solution
  5. customrecrystallizing the remaining oily product from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-baaa3c427b084013b72c2aed22a11d74
Quelldatensatz
uspto-grants-1987_09
Patentnummer
US04696759

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