Phenylacetyl chloride → 4'-Chloro-2-phenylacetophenone

HRID 978154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 978154
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-]>Cl>[CH2:7]([C:8]([C:15]1[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=1)=[O:9])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 7679Phenylacetyl chlorideHCID 7964ChlorobenzeneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 2338404'-Chloro-2-phenylacetophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a 2 liter 4 necked flask equipped with a mechanical stirrer thermometer, and reflux condensor was added 155 g (1.0 mole) of phenyl acetyl chloride and 500 ml (4.9 mole) of chlorobenzene. A total of 145 g (1.08 mole) of anhydrous aluminum chloride was added portionwise over 10 minutes. The mixture self warmed to 55° C. and evolved HCl gas over the course of the next 30 minutes. The mixture was stirred at about 50° C. for an additional 30 minutes and then poured onto about 500 g of ice and 110 ml of concentrated aqueous HCl. The organic layer (lower) was separated and the aqueous layer was washed with ethyl ether. The combined organic layers were washed with water, dilute aqueous NaOH, and water and then concentrated in vacuo. The resulting crude solid was recrystallized from 2200 ml of hexane yielding 132 g of 4-chlorophenyl benzyl ketone, mp 85°-90° C.

Aufarbeitung

  1. temperaturereflux condensor
  2. customover the course of the next 30 minutes
  3. customThe organic layer (lower) was separated
  4. washthe aqueous layer was washed with ethyl ether
  5. washThe combined organic layers were washed with water, dilute aqueous NaOH, and water
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude solid was recrystallized from 2200 ml of hexane yielding 132 g of 4-chlorophenyl benzyl ketone, mp 85°-90° C.

Quellen und Nachweise

ORD-Eintrag
ord-cca8bc29a9d74270ae0aab1afeea75b6
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04663341

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