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
additionto room temperature then poured in ice
extractionThe aqueous phase was extracted with methylene chloride which
customwas dried on magnesium sulfate
customvacuum evaporated

Sources & evidence

ORD record: ord-d63a34b3f064470a8369c2b0156b97c1
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106097B2

Reaction notes

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