Ethylene Glycol → 1-(4-Bromophenyl)cyclopropane-1-carboxylic acid

HRID 51767

Reaktionsgleichung

Reaktionsgleichung von HRID 51767
[OH-:1].[K+].C(O)C[OH:5].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:17]#N)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.Cl>O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([C:17]([OH:5])=[O:1])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1

Komponenten

6

Edukt 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 27952731-(4-Bromophenyl)Cyclopropanecarbonitrile2×

Produkt 1

HCID 162279661-(4-Bromophenyl)cyclopropane-1-carboxylic acidAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
137.5 °C

Versuchsvorschrift

To a solution of KOH (6.06 g, 0.11 mol) in 10 mL of H2O was added 40 mL of ethylene glycol and 1-(4-bromophenyl)-cyclopropanecarbonitrile (Intermediate 113, 10.0 g, 0.45 mol). This solution was heated to 135-140° C. for 4 h, cooled to room temperature, and then poured into a mixture of 100 mL ice and 10% aqueous HCl. The resulting mixture was allowed to stand overnight at 5° C., the solid was collected by filtration and washed with H2O. The colorless solid was dried under reduced pressure to give 10.6 g (97%) of the title compound.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationthe solid was collected by filtration
  3. washwashed with H2O
  4. customThe colorless solid was dried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6b418ab4484245439cbbd6ac784e0b57
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713647B2

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