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Sodium hydride → Methyl 3-(2'-chloro-4'-trifluoromethylphenoxy)-benzoxyacetate

HRID 1252650
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1252650
[H-].[Na+].[Cl:3][C:4]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH2:10][OH:11].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26]>O1CCCC1>[Cl:3][C:4]1[CH:18]=[C:17]([C:19]([F:21])([F:20])[F:22])[CH:16]=[CH:15][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH2:10][O:11][CH2:24][C:25]([O:27][CH3:28])=[O:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 130906883-(2'-Chloro-4'-trifluoromethylphenoxy)-benzyl alcohol

Produkt 1

HCID 13090689Methyl 3-(2'-chloro-4'-trifluoromethylphenoxy)-benzoxyacetateAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

3.25 parts by weight of 80% strength sodium hydride were suspended in 100 parts by volume of absolute tetrahydrofuran and a solution of 30 parts by weight of 3-(2'-chloro-4'-trifluoromethylphenoxy)-benzyl alcohol in 50 parts by volume of absolute tetrahydrofuran was then added, a little at a time. The mixture was stirred at 40° C. for half an hour and a solution of 15 parts by weight of methyl bromoacetate in 50 parts by volume of absolute tetrahydrofuran was added. The reaction mixture was then stirred at the boil for 2 hours, and was cooled and concentrated under reduced pressure. The oily residue was taken up in ether, and the organic phase was extracted with water, dried with magnesium sulfate and evaporated down under reduced pressure. Fractional distillation of the residue gave 19 parts by weight (51% of theory) of methyl 3-(2'-chloro-4'-trifluoromethylphenoxy)-benzoxyacetate (compound No. 4) of boiling point 150°-160° C./0.2 bar and refractive index nD25 : 1.5268.

Aufarbeitung

  1. stirringThe reaction mixture was then stirred at the boil for 2 hours
  2. temperaturewas cooled
  3. concentrationconcentrated under reduced pressure
  4. extractionthe organic phase was extracted with water
  5. dry with materialdried with magnesium sulfate
  6. customevaporated down under reduced pressure
  7. distillationFractional distillation of the residue

Quellen und Nachweise

ORD-Eintrag
ord-d7a7de992036447ca7428ab82af59cff
Quelldatensatz
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04744812

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