Water → 1-Phenylcyclobutanecarboxylic acid

HRID 1408524

Reaktionsgleichung

Reaktionsgleichung von HRID 1408524
[C:1]1([C:7]2([C:11]#N)[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:13].[K+].C1(C)C=CC=CC=1.[OH2:22]>C(O)CO>[C:1]1([C:7]2([C:11]([OH:22])=[O:13])[CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1140TolueneHCID 14797Potassium HydroxideHCID 844001-Phenylcyclobutanecarbonitrile

Produkt 1

HCID 2771711-Phenylcyclobutanecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

Intermediate 60 (2.6 g, 16.54 mmol) was dissolved in ethyleneglycol and added potassium hydroxide (5.6 g, 99.2 mmol). This mixture was heated to 160° C. for 2 h. After two hours reaction mixture was cooled to rt and toluene and water were added. Aqueous layer separated and acidified with HCl and pH adjusted to 4. Aqueous layer extracted with ethyl acetate and ethyl acetate layer was dried on anhydrous sodium sulphate. Ethyl acetate removed on rotavapour to obtain the title compound (930 mg) as a white solid.

Aufarbeitung

  1. customAfter two hours reaction mixture
  2. temperaturewas cooled to rt
  3. customAqueous layer separated
  4. extractionAqueous layer extracted with ethyl acetate and ethyl acetate layer
  5. dry with materialwas dried on anhydrous sodium sulphate
  6. customEthyl acetate removed on rotavapour

Quellen und Nachweise

ORD-Eintrag
ord-71aa019d0ba2401fabddd4773ae55d49
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921364B2

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