Hydrochloric Acid → Phenylacetic Acid

HRID 27809

Reaktionsgleichung

Reaktionsgleichung von HRID 27809
[C:1]1([CH2:7][C:8]([O:10]CC2C=CC=CC=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-].Cl>[N+](C)([O-])=O>[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 60999Benzyl phenylacetateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 999Phenylacetic AcidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6375NitromethaneLösungsmittel

Versuchsvorschrift

A mixture of benzyl phenylacetate (218 mg), methylene chloride (2 ml), aluminum chloride (357 mg), and nitromethane (1 ml) is stirred for 1 hour under ice cooling. The mixture is acidified with cold dilute hydrochloric acid and extracted with methylene chloride. The organic layer is extracted again with 5% aqueous sodium hydrogen carbonate solution. The aqueous extract is acidified with hydrochloric acid, and extracted with ethyl acetate. The organic layer is dried over sodium sulfate and concentrated to give phenylacetic acid (114 mg) melting at 77° C. Yield: 87%.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. extractionThe organic layer is extracted again with 5% aqueous sodium hydrogen carbonate solution
  3. extractionThe aqueous extract
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-052b6611baf54db8aba7f13890d7e39c
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04223132

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