Hydrochloric Acid → (RS)-Naproxen methyl ester

HRID 1030851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1030851
Br[C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:7]2.[C:19]1(C)C=C(C)C=C(C)C=1.Cl>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:13][O:12][C:11]1[CH:2]=[C:3]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([CH:14]([CH3:18])[C:15]([O:17][CH3:19])=[O:16])[CH:5]=[CH:4]2

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 7947MesityleneHCID 1196952-(5-Bromo-6-methoxynaphthalen-2-yl)propanoic acid

Produkt 1

HCID 529084(RS)-Naproxen methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

16.1 Grams of the methyl ester of the 2-(5-bromo-6-methoxy-2-naphthyl)propionic acid are dissolved in 65 ml of methylene chloride and then 10.4 ml of mesitylene and 12 ml of anhydrous titanium tetrachloride are added while keeping the temperature at about 20° C. The reaction mixture is kept under stirring at room temperature for 80 hours and then is poured into a mixture made of 68 g of crushed ice and of 15 ml of a 35% (w/v) aqueous solution of hydrochloric acid. The layers are separated after 15 minutes of stirring, the aqueous layer is extracted with 30 ml of methylene chloride and then is discarded. The organic layers are collected, first washed with 50 ml of a 1N aqueous solution of hydrochloric acid, then with 50 ml of water and lastly with 50 ml of a 8% (w/v) aqueous solution of sodium bicarbonate. The organic solution is dried over anhydrous sodium sulfate and then is evaporated under vacuum. The residue is crystallized first with n-hexane and then with methyl alcohol obtaining 4 g of product with a yield equal to 32.7%.

Aufarbeitung

  1. customat about 20° C
  2. additionis poured into a mixture
  3. customThe layers are separated after 15 minutes
  4. stirringof stirring
  5. extractionthe aqueous layer is extracted with 30 ml of methylene chloride
  6. customThe organic layers are collected
  7. washfirst washed with 50 ml of a 1N aqueous solution of hydrochloric acid
  8. dry with materialThe organic solution is dried over anhydrous sodium sulfate
  9. customis evaporated under vacuum
  10. customThe residue is crystallized first with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-c4107deb291f45f78864f34a668e7a4f
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05107013

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