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4-Chlorophenol → 1-Chloro-4-(2-chloroethoxy)benzene

HRID 1032855
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1032855
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1S(N)(=O)=O.[Cl:15]C1C=CC(O)=CC=1.C1(=O)OCCO1.OCCOC1C=CC(Cl)=CC=1.C(Cl)(Cl)=O.S(Cl)(Cl)=O>>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:15])=[CH:7][CH:6]=1
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Komponenten

7

Edukt 6

HCID 46844-ChlorophenolHCID 6371PhosgeneHCID 7303Ethylene carbonateHCID 159072-(4-Chlorophenoxy)ethanolHCID 24386Thionyl ChlorideHCID 137294542-(2-Chloroethoxy)benzene-1-sulfonamide

Produkt 1

HCID 83034
1-Chloro-4-(2-chloroethoxy)benzene

Versuchsvorschrift

A process for the preparation of 2-(2-chloroethoxy)-benzenesulfonamide of formula I ##STR15## which process comprises the etherification of 4-chlorophenol of formula II ##STR16## with ethylene carbonate at a temperature between +130° C. and +150° C. and chlorination of the resulting 4-(2-hydroxyethoxy)-chlorobenzene of formula III ##STR17## with phosgene or thionyl chloride at a temperature between +70° C. and +90° C. to give 4-(2-chloroethoxy)-chlorobenzene of formula IV ##STR18## which is converted with chlorosulfonic acid, at a temperature between -20° C. and +60° C. and subsequent neutralizaion with sodium hydroxide to the sulfonic acid sodium salt of formula V ##STR19## which is hydrogenated at a temperature between +20° C. and +70° C. to the compound of formula VI ##STR20## which is subsequently reacted with phosgene at a temperature between +60° C. and +120° C. to the sulfonic acid chloride of formula VII ##STR21## which is reacted with ammonia at a temperature between 0° C. and +100° C. to the sulfonamide of formula I.

Aufarbeitung

  1. customat a temperature between +70° C. and +90° C.

Quellen und Nachweise

ORD-Eintrag
ord-9d6f71393fab4efa83bf6fe72ca1d068
Quelldatensatz
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04959501

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