Diethyl Ether → 4-(4-Propylcyclohexyl)phenyl 4-ethoxy-2,3-difluorobenzoate

HRID 1265957

Reaktionsgleichung

Reaktionsgleichung von HRID 1265957
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].C(OCC)C.[F:22][C:23]1[C:31]([F:32])=[C:30]([O:33][CH2:34][CH3:35])[CH:29]=[CH:28][C:24]=1[C:25](O)=[O:26]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:34]([O:33][C:30]1[CH:29]=[CH:28][C:24]([C:25]([O:16][C:13]2[CH:14]=[CH:15][C:10]([CH:7]3[CH2:6][CH2:5][CH:4]([CH2:1][CH2:2][CH3:3])[CH2:9][CH2:8]3)=[CH:11][CH:12]=2)=[O:26])=[C:23]([F:22])[C:31]=1[F:32])[CH3:35]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 27694004-Ethoxy-2,3-difluorobenzoic acidHCID 3126231Phenol, 4-(trans-4-propylcyclohexyl)-

Produkt 1

HCID 185473774-(4-Propylcyclohexyl)phenyl 4-ethoxy-2,3-difluorobenzoateAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

In a 1 L three-neck flask, 6.60 g of 2,3-difluoro-4-ethoxybenzoic acid (a) and 7.06 g of 4-(4-propyl-1-cyclohexyl)phenol (b) were dissolved in 450 mL of methylene chloride. 4.09 g of 4-dimethylaminopyridine was added thereto and stirred for 1 hour at room temperature. A solution of 7.60 g of N,N-dicyclohexylcarbodiimide dissolved in 195 mL of methylene chloride was added thereto and stirred overnight. Then diethyl ether was added and the precipitated urea was filtered off, saturated aqueous solution of sodium chloride was added and was stirred for 1 hour. The organic layer separated was washed with 3N hydrochloric acid and saturated aqueous solution of sodium bicarbonate, and was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 13.1 g of 4-(4-propylcyclohexyl)phenyl 4-ethoxy-2,3-difluorobenzoate (c).

Aufarbeitung

  1. additionwas added
  2. stirringstirred overnight
  3. filtrationthe precipitated urea was filtered off
  4. additionsaturated aqueous solution of sodium chloride was added
  5. stirringwas stirred for 1 hour
  6. customThe organic layer separated
  7. washwas washed with 3N hydrochloric acid and saturated aqueous solution of sodium bicarbonate
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-00407b0771fc49628122da01bf290b5b
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06548126B1

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