Reaktion #165488

Reaktionsgleichung

4-(3-carboxy-4-hydroxyphenoxy)-1-nitrobenzene

2,5-dihydroxybenzoic acid

K2CO3

dimethyl sulfate

→

4-(3-methoxycarbonyl-4-methoxyphenoxy)-1-nitrobenzene

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was heated at the reflux temp
2. 2
   Temperaturovernight, then cooled to room temp.
3. 3
   Filtrationfiltered through a pad of Celite®
4. 4
   EinengenThe resulting solution was concentrated under reduced pressure
5. 5
   Sonstigeabsorbed onto SiO2
6. 6
   Sonstigepurified by column chromatography (50% EtOAc/50% hexane)

Vorschrift

To a solution of 4-(3-carboxy-4-hydroxyphenoxy)-1-nitrobenzene (prepared from 2,5-dihydroxybenzoic acid in a manner analogous to that described in Method A13, Step 1, 12 mmol) in acetone (50 mL) was added K2CO3 (5 g) and dimethyl sulfate (3.5 mL). The resulting mixture was heated at the reflux temp. overnight, then cooled to room temp. and filtered through a pad of Celite®. The resulting solution was concentrated under reduced pressure, absorbed onto SiO2, and purified by column chromatography (50% EtOAc/50% hexane) to give 4-(3-methoxycarbonyl-4-methoxyphenoxy)-1-nitrobenzene as a yellow powder (3 g): mp 115-118° C.

Quelle