p-Toluenesulfonic acid → HCID 22734358, Verbindung

HRID 1057936

Reaktionsgleichung

Reaktionsgleichung von HRID 1057936
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:5]([OH:6])[C:4]=1[OH:10].[C:11]1(=O)[CH2:15][CH2:14][CH2:13][CH2:12]1.C([O-])([O-])OC.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:10][C:11]3([O:6][C:5]=2[CH:7]=[CH:8][CH:9]=1)[CH2:15][CH2:14][CH2:13][CH2:12]3

Komponenten

7

Edukt 5

HCID 6101p-Toluenesulfonic acidHCID 8452CyclopentanoneHCID 136223-MethoxycatecholHCID 14798Sodium HydroxideHCID 53629101Methylorthoformate

Produkt 1

HCID 22734358HCID 22734358, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A mixture of 3-methoxycatechol (22.6 g), cyclopentanone (27.1 g), methyl orthoformate (34.2 g), p-toluenesulfonic acid.monohydrate (0.2 g), and benzene (300 ml) was heated under reflux for 24 hours. After being allowed to stand for cooling, a dilute solution of sodium hydroxide was added to the mixture followed by extraction with ether. The organic layer was washed with a saturated saline and dried over anhydrous potassium carbonate. The solvent was distilled off under reduced pressure to give Compound IIax-a (30 g, 90%) as a colorless oily substance.

Aufarbeitung

  1. temperatureunder reflux for 24 hours
  2. temperaturefor cooling
  3. extractionfollowed by extraction with ether
  4. washThe organic layer was washed with a saturated saline
  5. dry with materialdried over anhydrous potassium carbonate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto give Compound IIax-a (30 g, 90%) as a colorless oily substance

Quellen und Nachweise

ORD-Eintrag
ord-90aaaece27484cfd9e92e5e5afb4e018
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514996B2

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