Phenylacetyl chloride → 4'-Chloro-2-phenylacetophenone

HRID 1607203Notes

Reaction equation

[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

Participants

Conditions

Temperature: 44 °C

Procedure

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 44° 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 recrystalized from 2200 ml of hexane yielding 132 g of 4-chlorophenyl benzyl ketone, mp 85°-90° C. NMR data was consistent with the structure.

Workup

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

Sources & evidence

ORD record: ord-f2d1e2ee39494febb6776b5dbb5c1722
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863947

Reaction notes

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