Hydrochloric Acid → 1-Hydroxy-3-methyl-1-(4-nitrophenyl)-6-methoxyisochroman

HRID 2179887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179887
[CH3:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:12][CH3:13])[CH:9]=2)[CH:4]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[O:3]1.[OH-:23].[Na+].Cl>CS(C)=O.CN(C=O)C>[OH:23][C:4]1([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[C:5]2[C:10](=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2)[CH2:11][CH:2]([CH3:1])[O:3]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 224889743-Methyl-1-(4-nitrophenyl)-6-methoxyisochroman

Produkt 1

HCID 224889711-Hydroxy-3-methyl-1-(4-nitrophenyl)-6-methoxyisochroman

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3 (1.3 g) in 4 ml of DMSO and 24 ml of DMF was cooled to 8-12° C. and air was passed through the mixture. To the solution was added 1.2 ml of 50% aqueous sodium hydroxide in one portion and the resulting mixture was stirred for 5 hours. HCl (1 N) was added, and extracted with ethyl acetate three times. The combined organic phase was washed with water in order to remove DMF, dried over Na2SO4. Removal of the solvent afforded syrup crude product (1.6 g), which was used directly for the next step.

Aufarbeitung

  1. extractionextracted with ethyl acetate three times
  2. washThe combined organic phase was washed with water in order
  3. customto remove DMF
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-707090167f8a43f1941721a79a3024ae
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06887867B2

Notizen zur Reaktion

Wird geladen…