Methyl iodide → Methyl 6-Methoxybenzo[d][1,3]dioxole-5-carboxylate

HRID 1598980

Reaktionsgleichung

Reaktionsgleichung von HRID 1598980
[OH:1][C:2]1[C:3]([C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[H-].[Na+].I[CH3:18]>CN(C=O)C>[CH3:18][O:1][C:2]1[C:3]([C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 590804Methyl 6-hydroxy-1,3-benzodioxole-5-carboxylate

Produkt 1

HCID 18931116Methyl 6-Methoxybenzo[d][1,3]dioxole-5-carboxylateAusbeute 107,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of methyl 6-hydroxy-1,3-benzodioxole-5-carboxylate (2.7 g, 14 mmol), sodium hydride (456 mg, 19 mmol, 760 mg of a 60% dispersion in mineral oil), iodomethane (1.9 g, 13 mmol) and DMF (approximately 35 mL) was stirred 2 hours. The mixture was poured into ice-water and the mixture was extracted with diethyl ether (2×). The combined extracts were washed with water (3×) and brine (1×) and concentrated to give methyl 6-methoxy-1,3-benzodioxole-5-carboxylate (3 g, 14 mmol), m.p. 74°-75° C.

Aufarbeitung

  1. extractionthe mixture was extracted with diethyl ether (2×)
  2. washThe combined extracts were washed with water (3×) and brine (1×)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a03c5294016e49e8afa327dffc63d387
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739336

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