Aluminum(III) Chloride → 1-(4-Chloro-2-hydroxyphenyl)ethanone

Reaction equation

[OH:1][C:2]1[CH:7]=[C:6](OC(C(OCC)=O)(C)C)[CH:5]=[CH:4][C:3]=1[C:17](=[O:19])[CH3:18].[Cl-:20].[Al+3].[Cl-].[Cl-]>>[Cl:20][C:6]1[CH:5]=[CH:4][C:3]([C:17](=[O:19])[CH3:18])=[C:2]([OH:1])[CH:7]=1

Participants

Reactant 2

HCID 6451240Aluminum(III) Chloride

HCID 577628812'-Hydroxy-4'-(ethoxycarbonyldimethylmethoxy)acetophenone2×

Product 1

HCID 10515131-(4-Chloro-2-hydroxyphenyl)ethanone

Conditions

Temperature: 200 °C

Procedure

3-chlorophenyl acetate (starting material 2) was mixed with aluminium chloride (3 eq). The mixture was heated at 200° C. for 1 hour. The reaction medium was cooled to room temperature then poured in ice. The aqueous phase was extracted with methylene chloride which was dried on magnesium sulfate then vacuum evaporated.

Workup

temperatureThe reaction medium was cooled to room temperature
additionthen poured in ice
extractionThe aqueous phase was extracted with methylene chloride which
customwas dried on magnesium sulfate
customvacuum evaporated

Sources & evidence

ORD record: ord-5c461b7df70d40b1a5e16f14447e9a27
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058308B2

Reaction notes

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