Methyl chloroformate → 1-Methoxycarbonyloxy-2,4-dimethoxynaphthalene

HRID 466215

Reaktionsgleichung

Reaktionsgleichung von HRID 466215
[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].Cl[C:17]([O:19][CH3:20])=[O:18].C(N(CC)CC)C>O1CCCC1>[CH3:20][O:19][C:17]([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:18]

Komponenten

5

Edukt 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 125635471-Hydroxy-2,4-dimethoxynaphthalene

Produkt 1

HCID 141830431-Methoxycarbonyloxy-2,4-dimethoxynaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

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 was added 0.694 g of methyl chloroformate followed by 0.743 g of triethylamine. The mixture was stirred at room temperature for 16 hours, filtered, then the solvent removed under reduced pressure. The residue was dissolved in diethyl ether, washed with dilute hydrochloric acid and dried over anhydrous sodium sulfate. The ether was removed under reduced pressure and the residue chromatographed on silica gel, eluting with a 1:1 mixture of methylene chloride and hexane, to give 1-methoxycarbonyloxy-2,4-dimethoxynaphthalene, m.p. 128°-129° C.

Aufarbeitung

  1. filtrationfiltered
  2. customthe solvent removed under reduced pressure
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwashed with dilute hydrochloric acid
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ether was removed under reduced pressure
  7. customthe residue chromatographed on silica gel
  8. washeluting with a 1:1 mixture of methylene chloride and hexane

Quellen und Nachweise

ORD-Eintrag
ord-51a4826d03fb4eae92e228d814dc4a1d
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155132

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