3-Methoxybenzaldehyde → 1-Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furan

HRID 482298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 482298
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:10](=[O:11])[O:9][CH2:8]2.COC1C=C(C=CC=1)C=O.C1(P(=CC(OC)=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[OH:11][CH:10]1[C:12]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[CH2:8][O:9]1

Komponenten

5

Edukt 3

HCID 115693-MethoxybenzaldehydeHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 109865837-methoxy-3H-isobenzofuran-1-one

Produkt 1

HCID 136136891-Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furan

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

1Hydroxy-7-methoxy-1,3-dihydrobenzo[c]furan (1.08 g), which was prepared with using 7-methoxyphthalide which was synthesized with using 3-methoxybenzaldehyde by the method described in Journal of Organic Chemistry, 1980, 45, 1835-1838, was dissolved in Chloroform (20 ml). Methyl (Triphenylphosphoranylidene)acetate (2.68 g) was added to the solution. The mixture was stirred for 40 min. at 50° C. A temperature of the reaction mixture was down to room temperature. The reaction solution was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (1.25 g) having the following physical data.

Aufarbeitung

  1. customwas down to room temperature
  2. customThe reaction solution was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-3c136f74521f4e87b8ce46b1c969868a
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05795914

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