Water → 3-Acetyl-1-chloro-5-(3,3-dichloroprop-2-enyloxy)-2-hydroxybenzene

HRID 497044Notes

Reaction equation

[C:1]([C:4]1[C:5]([O:17]CC=C(Cl)Cl)=[C:6]([Cl:16])[CH:7]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([Cl:15])[Cl:14])[CH:9]=1)(=[O:3])[CH3:2].O>C1(C)C=CC=CC=1.C(OCC)C>[C:1]([C:4]1[C:5]([OH:17])=[C:6]([Cl:16])[CH:7]=[C:8]([O:10][CH2:11][CH:12]=[C:13]([Cl:15])[Cl:14])[CH:9]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 85 °C

Procedure

6.1 g of 3-acetyl-2,5-bis-(3,3-dichloroprop-2-enyloxy)-1-chlorobenzene were dissolved in 160 ml of toluene. 7.79 g of magnesium dibromide/diethyl ether complex, dissolved in 25 ml of diethyl ether, were added to this solution, and the mixture was then stirred at 85° C. for 6 hours. After the reaction had ended according to TLC, the mixture was allowed to cool, about 300 ml of water were added and the organic phase was separated off. The aqueous phase was re-extracted twice with ethyl acetate, and the combined organic phases were then washed with saturated sodium chloride solution. After drying and concentration of the organic phase, the crude product was purified chromatographically. Yield: 2.86 g (64%)

Workup

additionwere added to this solution
temperatureto cool
customthe organic phase was separated off
extractionThe aqueous phase was re-extracted twice with ethyl acetate
washthe combined organic phases were then washed with saturated sodium chloride solution
customAfter drying
customconcentration of the organic phase, the crude product was purified chromatographically

Sources & evidence

ORD record: ord-0f40cc90efa04e9faed0a5a8808594e6
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949551B2

Reaction notes

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