Ethylene → 2-Methoxy-6-vinylnaphthalene

HRID 482162

Reaktionsgleichung

Reaktionsgleichung von HRID 482162
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[CH:3]=1.[CH2:14](N(CC)CC)[CH3:15].C=C.[OH-].[Na+].Br.C(N(CC)CC)C>Cl[Pd]Cl.C(C(CC)=O)C>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([CH:14]=[CH2:15])[CH:11]=[CH:10]2

Komponenten

8

Edukt 5

HCID 6325EthyleneHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 787862-Bromo-6-methoxynaphthaleneHCID 2734074Triethylammonium bromide

Produkt 1

HCID 6035352-Methoxy-6-vinylnaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24290Palladium ChlorideKatalysatorHCID 7288Ethyl ketoneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

To a 5-gallon stainless steel electrically heated reactor is added 1,485 grams (6.26 mol) of 2-bromo-6-methoxynaphthalene (BMN) (produced as in Example 7 hereof, added as a dry powder through a 2" opening in the reactor head), 672 grams (6.64 mol) of triethylamine, 0.56 grams of PdCl2 (3.2 mmol) and 6.2 grams of NMDP (19 mmol). The reactor is purged three times with nitrogen (50 psig) and then three times with ethylene (50 psig). The reactor is charged with ethylene (about 300 psig) and then warmed at 95° C. Ethylene pressure in the reactor is raised to about 550 psig after reaching reaction temperature. When the reaction is completed, the reaction mixture is cooled to below 50° C. and the ethylene is vented. Diethyl ketone (3,835 g) is added to the reaction mixture. Aqueous sodium hydroxide (24.8 wt %) is then added to the reaction mixture to neutralize the triethylamine hydrobromide salt formed during the reaction. The aqueous phase is removed, as well as possible at this point, from the reactor. The reaction mixture is filtered using a medium porosity 3-liter sintered glass funnel and any further aqueous phase that separates is removed. The volatile organics (acetonitrile, diethyl ketone, triethylamine) are removed at reduced pressure (1 mm Hg, 45° C.) to give 6-methoxy-2-vinylnaphthalene as a yellow solid.

Aufarbeitung

  1. customproduced as in Example 7
  2. additionadded as a dry powder through a 2"
  3. customThe reactor is purged three times with nitrogen (50 psig)
  4. additionThe reactor is charged with ethylene (about 300 psig)
  5. temperatureEthylene pressure in the reactor is raised to about 550 psig
  6. customreaction temperature
  7. temperaturethe reaction mixture is cooled to below 50° C.
  8. customformed during the reaction
  9. customThe aqueous phase is removed
  10. filtrationThe reaction mixture is filtered
  11. customany further aqueous phase that separates is removed
  12. customThe volatile organics (acetonitrile, diethyl ketone, triethylamine) are removed at reduced pressure (1 mm Hg, 45° C.)

Quellen und Nachweise

ORD-Eintrag
ord-ed75f97fb4d04c68b12c8d5500858c77
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05792886

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