2,3-Dihydroxy-p-anisic acid → 7-methoxy-2',3',5',6'-tetrahydro-Spiro[1,3-benzodioxole-2,4'-(4H)-pyran]-4-carboxylic acid

HRID 2196088

Reaktionsgleichung

Reaktionsgleichung von HRID 2196088
[OH:1][C:2]1[C:10]([OH:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][O:15][C:16]1[CH2:21][CH2:20][O:19][CH2:18][CH:17]=1>C(OCC)(=O)C>[OH:1][C:2]1[C:10]([OH:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:13][O:12][C:9]1[C:14]2[O:15][C:16]3([O:1][C:2]=2[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=1)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3

Komponenten

5

Edukt 2

HCID 775342,3-Dihydroxy-p-anisic acidHCID 870513,6-dihydro-4-methoxy-2H-pyran

Produkt 2

HCID 775342,3-Dihydroxy-p-anisic acidHCID 592867287-methoxy-2',3',5',6'-tetrahydro-Spiro[1,3-benzodioxole-2,4'-(4H)-pyran]-4-carboxylic acidAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 2,3-dihydroxy-4-methoxybenzoic acid (6.04 g, 32.8 mmol) in 5,6-dihydro-4-methoxy-2H-pyran (20 mL, 152 mmol) was kept at 140° C. for three days. At room temperature ethyl acetate (200 mL) was added and the organic phase was extracted with saturated aqueous NaHCO3 (2×50 mL). The aqueous phase was washed with Et2O (2×40 mL), acidified to pH=1 with concentrated HCl and extracted with dichloromethane (2×50 mL). The organic phase was dried over MgSO4. Evaporation under reduced pressure afforded traces of 2,3-dihydroxy-4-methoxybenzoic acid along with 7-methoxy-2′,3′,5′,6′-tetrahydro-Spiro[1,3-benzodioxole-2,4′-(4H)-pyran]-4-carboxylic acid (1.23 g, 14%). 13C NMR (DMSO) δ 164.9, 148.2, 146.6, 134.5, 123.7, 117.0, 107.1, 106.8, 64.4, 56.0, 35.3.

Aufarbeitung

  1. extractionthe organic phase was extracted with saturated aqueous NaHCO3 (2×50 mL)
  2. washThe aqueous phase was washed with Et2O (2×40 mL)
  3. extractionextracted with dichloromethane (2×50 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customEvaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-153adc409b63492581600d91c122b8bb
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338431B2

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