Sulfuric Acid → Methyl 6-hydroxy-1,3-benzodioxole-5-carboxylate

HRID 1598979

Reaktionsgleichung

Reaktionsgleichung von HRID 1598979
N[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.S(=O)(=O)(O)[OH:16].N([O-])=O.[Na+]>O>[OH:16][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 1118Sulfuric AcidHCID 290838Methyl 6-amino-1,3-benzodioxole-5-carboxylateHCID 23668193Sodium Nitrite

Produkt 1

HCID 590804Methyl 6-hydroxy-1,3-benzodioxole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel4×

Versuchsvorschrift

A mixture of methyl 6-amino-1,3-benzodioxole-5-carboxylate (6.3 g, 32 mmol), concentrated sulfuric acid (7 mL) and water (35 mL) was cooled in an ice-bath and then a mixture of sodium nitrite (2.3 g, 33 mmol) and water (15 mL) was added. The mixture was diluted with 50 mL of water and added to a boiling solution of cupric sulfate pentahydrate (35 g, 140 mmol) and water (75 mL). The mixture was heated 10 minutes at boiling and then cooled in an ice-bath and extracted with diethyl ether (3×). The combined extracts were washed with water (4×) and brine (1×), dried. (K2CO3) and concentrated. The residue was purified by column chromatography eluting with hexane/ethyl acetate (98:2-97:3) to give methyl 6-hydroxy-1,3-benzodioxole-5-carboxylate (2.7 g, 14 mmol), m.p. 100°-101° C.

Aufarbeitung

  1. temperaturewas cooled in an ice-bath
  2. additionwas added
  3. temperatureThe mixture was heated 10 minutes
  4. temperaturecooled in an ice-bath
  5. extractionextracted with diethyl ether (3×)
  6. washThe combined extracts were washed with water (4×) and brine (1×)
  7. customdried
  8. concentration(K2CO3) and concentrated
  9. customThe residue was purified by column chromatography
  10. washeluting with hexane/ethyl acetate (98:2-97:3)

Quellen und Nachweise

ORD-Eintrag
ord-15553412c6774a62915868fee6c6b7f3
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739336

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