1,2-Dibromoethane → Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate

HRID 596602

Reaktionsgleichung

Reaktionsgleichung von HRID 596602
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([OH:11])[CH:5]=1.C[O-].[Na+].Br[CH2:17][CH2:18]Br>CO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:17][CH2:18][O:11][C:6]=2[CH:5]=1

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 287064Methyl 3,4-DihydroxybenzoateHCID 10942334Sodium Methoxide

Produkt 1

HCID 3802178Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 4.20 g. of 3,4-dihydroxybenzoic acid methyl ester in 10.0 ml. of methanol is combined with 7.0 g. of sodium methoxide and then 15.0 g. of 1,2-dibromoethane is added. The resulting mixture is refluxed under nitrogen for 24 hours, then cooled, filtered, evaporated in vacuo and the resulting oil dissolved in 50 ml. of chloroform. The resulting solution after again filtering is chromatographed over 100 ml. of silica gel eluting with chloroform to obtain 3,4-ethylenedioxybenzoic acid methyl ester, m.p. 43°-45° C.

Aufarbeitung

  1. temperatureThe resulting mixture is refluxed under nitrogen for 24 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. dissolutionthe resulting oil dissolved in 50 ml
  6. filtrationThe resulting solution after again filtering
  7. customis chromatographed over 100 ml

Quellen und Nachweise

ORD-Eintrag
ord-a68d6c679ea04501b26a9aae8c2ed78d
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011323

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