Pyridine → 1-Chlorocarbonyloxy-2,4-dimethoxynaphthalene

HRID 466214

Reaktionsgleichung

Reaktionsgleichung von HRID 466214
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[O:14][CH3:15].N1C=CC=CC=1.[C:22](Cl)([Cl:24])=[O:23]>O1CCCC1.C1C=CC=CC=1>[Cl:24][C:22]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][C:3]=1[O:14][CH3:15])=[O:23]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 6371PhosgeneHCID 125635471-Hydroxy-2,4-dimethoxynaphthalene

Produkt 1

HCID 198727301-Chlorocarbonyloxy-2,4-dimethoxynaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 1.27 g of 1-hydroxy-2,4-dimethoxynaphthalene, prepared as shown in Preparations 7 and 8, in 50 ml of tetrahydrofuran and 1 ml of pyridine is added 10 ml of a solution of 12.5% phosgene in benzene. The mixture is stirred overnight at 25° C., filtered and the filtrate evaporated under vacuum to afford crude 1-chlorocarbonyloxy-2,4-dimethoxynaphthalene. This chloroformate is dissolved in 50 ml of dry tetrahydrofuran and a solution of 1.14 g of diethylamine in 10 ml of tetrahydrofuran added. After 4 hours at room temperature the reaction mixture is diluted with ethyl acetate and washed with dilute hydrochloric acid. The organic phase is dried over sodium sulfate and solvent removed under reduced pressure to yield 1-diethylcarbamoyloxy-2,4-dimethoxynaphthalene.

Aufarbeitung

  1. filtrationfiltered
  2. customthe filtrate evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ae719fbd2b7941a5bd62c52095c67ff3
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155132

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