Ethyl bromoacetate → 2-(Carboxymethoxy)thioxanthone

HRID 1062322

Reaktionsgleichung

Reaktionsgleichung von HRID 1062322
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.Br[CH2:18][C:19]([O:21]CC)=[O:20]>>[C:19]([CH2:18][O:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1)([OH:21])=[O:20]

Komponenten

3

Versuchsvorschrift

An example of a conventional synthetic route to 2-carboxymethoxythioxanthone involves three stages. Firstly, phenol is reacted with dithiobisbenzoic acid to produce 2-hydroxythioxanthone in a 60% yield. Secondly, the 2-hydroxythioxanthone is reacted with ethyl bromoacetate to produce the ethyl ester of 2-carboxymethoxythioxanthone in 75% yield. Thirdly, the ester is hydrolysed by acidification to produce the desired product in 90% yield. These three stages form an inefficient and time-consuming process to provide a product that is a dark colour, contains impurities and by-products and is produced with only an overall yield of 40% from the starting material.

Quellen und Nachweise

ORD-Eintrag
ord-e782f4331ec0437b9f66ccd6ca7fc05c
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960668B2

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