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-2dd3cc31c5c841f7bbcf611a0e989be6
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566737B2

Reaction notes

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