4-Nitrobenzaldehyde → 3-Methyl-1-(4-nitrophenyl)-6-methoxyisochroman

HRID 2179886Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179886
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([OH:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)([O-:15])=[O:14]>Cl.O1CCOCC1>[CH3:11][CH:10]1[CH2:9][C:5]2[C:6](=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:20]([C:19]2[CH:22]=[CH:23][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)[O:12]1

Komponenten

5

Edukt 2

HCID 5414-NitrobenzaldehydeHCID 124998521-(3-Methoxyphenyl)propan-2-ol

Produkt 1

HCID 224889743-Methyl-1-(4-nitrophenyl)-6-methoxyisochromanAusbeute 93,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(3′-methoxyphenyl)-2-propyl alcohol 2 (0.98 g, 5.8 mmol) in 25 ml of HCl solution in 1,4-dioxane was added 4-nitrobenzaldehyde (0.91 g, 6.0 mmol) in one portion. The solution was refluxed for 4 hours. After removing the solvent under reduced pressure, the residue was washed with cold ethanol three times, affording the product 3 (1.62 g, yield 90%). 1HNMR(CDCl3): 8.20 (d, J=8.7 Hz, 2H), 7.50 (d, J=8,7 Hz, 2H), 6.65-6.48 (m, 3H), 5.78 (s, 1H), 4.01 (m, 1H), 3.76 (s, 3H), 2.80 (m, 2H), 1.40 (d, J=6.1 Hz).

Aufarbeitung

  1. temperatureThe solution was refluxed for 4 hours
  2. customAfter removing the solvent under reduced pressure
  3. washthe residue was washed with cold ethanol three times

Quellen und Nachweise

ORD-Eintrag
ord-6954d58a089a47eaa1d77e8fcdc9c8d5
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06887867B2

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