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Iodine → 6-[3-(1,1-Dimethyldecyl)-4-methoxyphenyl]-2-naphthoic acid

HRID 249065
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 249065
[CH3:1][C:2]([C:13]1[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=1[O:20][CH3:21])([CH3:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Mg].II.Br[C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[CH:32]=[C:31]([C:36]([O:38]C)=[O:37])[CH:30]=[CH:29]2>C1COCC1.[Cl-].[Zn+2].[Cl-].O>[CH3:1][C:2]([C:13]1[CH:18]=[C:17]([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[CH:32]=[C:31]([C:36]([OH:38])=[O:37])[CH:30]=[CH:29]3)[CH:16]=[CH:15][C:14]=1[O:20][CH3:21])([CH3:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 807IodineHCID 8541342-Bromo-6-methoxycarbonylnaphthaleneHCID 5462224MagnesiumHCID 136335572-(1,1-Dimethyldecyl)-4-bromo anisole

Produkt 1

HCID 189527686-[3-(1,1-Dimethyldecyl)-4-methoxyphenyl]-2-naphthoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855
Zincchloride
Katalysator
HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 16 g (45 mmol) of 2-(1,1-dimethyldecyl)-4-bromo anisole in 60 ml of THF is slowly added to of magnesium and a crystal of iodine. The mixture is slightly heated at the beginning of the addition until the reaction of formation of the Grignard is initiated. Then the remainder of the solution containing the brominated derivative is added in a manner to maintain a regular reflux. Once the addition is complete, the mixture is stirred for 30 minutes at 50° C. and then cooled to ambient temperature. 7.4 g (54 mmol) of zinc chloride in solution in 50 ml of THF are added. The mixture is stirred for 30 minutes at ambient temperature, 6.6 g (25 mmol) of methyl 6-bromo-2-naphthoate are added and then 175 mg of NiCl2 /DPPE complex. The mixture is stirred for 3 hours at ambient temperature at which point 250 ml of water are added. The THF is evaporated under reduced pressure and the residue is extracted with dichloromethane, dried and the solvent evaporated. The residue is purified by passage through a silica column (eluant: mixture of 60% dichloromethane and 40% hexane). On evaporation, a solid is obtained which is recrystallized twice in hexane to give the methyl ester of 6-[3-(1,1-dimethyldecyl)-4-methoxyphenyl]-2-naphthoic acid: 7.05 g (61%). Melting point: 92° C.

Aufarbeitung

  1. temperatureThe mixture is slightly heated at the beginning of the addition until the reaction of formation of the Grignard
  2. additionThen the remainder of the solution containing the brominated derivative
  3. additionis added in a manner
  4. temperatureto maintain a regular reflux
  5. additionOnce the addition
  6. temperaturecooled to ambient temperature
  7. stirringThe mixture is stirred for 30 minutes at ambient temperature
  8. stirringThe mixture is stirred for 3 hours at ambient temperature at which
  9. additionare added
  10. customThe THF is evaporated under reduced pressure
  11. extractionthe residue is extracted with dichloromethane
  12. customdried
  13. customthe solvent evaporated
  14. customThe residue is purified by passage through a silica column (eluant: mixture of 60% dichloromethane and 40% hexane)
  15. customOn evaporation
  16. customa solid is obtained which
  17. customis recrystallized twice in hexane

Quellen und Nachweise

ORD-Eintrag
ord-5b904146c0d04793acb5671939f399f7
Quelldatensatz
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05212303

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