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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1382186Erstellt: 26. Oktober 2026

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

https://huagongshe.com/reaction/1382186

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt4-ChlorophenolHCID 4684—
EduktPhosgeneHCID 6371—
EduktEthylene carbonateHCID 7303—
Edukt2-(2-Chlorophenoxy)ethanolHCID 84933—
Edukt2-(2-Chloroethoxy)benzene-1-sulfonamideHCID 13729454—
Produkt1-Chloro-2-(2-chloroethoxy)benzeneHCID 21890669—

Reaktionsschritte

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 2-(2-hydroxyethoxy)-chlorobenzene of formula III ##STR17## with phosgene at a temperature between +70° C. and +90° C. to give 2-(2-chloroethoxy)-chlorobenzene of formula IV ##STR18## which is converted with chlorosulfonic acid, at a temperature between +20° C. and +60° C. and subsequent neutralization 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 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.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS04806528
Quelldatensatzuspto-grants-1989_02
ORD IDord-8348253b0f0d45ae8dee46a913a05850
Quellennotizuspto-grants-1989_02