Water → Phthalaldehyde

HRID 1706050

Reaktionsgleichung

Reaktionsgleichung von HRID 1706050
Br[CH:2](Br)[C:3]1C(C(Br)Br)=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:13]([O-:16])(=O)[CH3:14].[Na+].C(=O)([O-])[O-:19].[Ca+2].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH:7]1[CH:8]=[C:3]([CH:2]=[O:19])[C:14]([CH:13]=[O:16])=[CH:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10112Calcium CarbonateHCID 832341,2-Bis(dibromomethyl)benzeneHCID 517045Sodium Acetate

Produkt 1

HCID 4807PhthalaldehydeAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

With efficient stirring, a suspension consisting of 10 g (23.7 mmols) of α,α,α',α'-tetrabromo-o-xylene, 9.7 g (118 mmols) of sodium acetate. 1.74 g (5.4 mmols) of tetrabutylammonium bromide, 4.75 g of calcium carbonate and 10 ml of distilled water is heated to reflux in a nitrogen atmosphere, whereupon the temperature rises to 118° C. After a reaction time of 6 hours, the reaction mixture is cooled and, after the addition of 50 ml of ethyl acetate, filtered. The organic phase is separated in a separating funnel and the aqueous phase is washed once more with ethyl acetate. The combined organic extracts (ethyl acetate extracts) are washed with a solution of sodium chloride, dried over magnesium sulfate and then concentrated in vacuo. The residue is taken up in 40 ml of toluene and the solution is purified by chromatography through a column packed with 100 g of silica gel. After elution with toluene, concentration of the eluate yields 2.10 g (66.2% of theory) of o-phthalaldehyde with a melting point of 53°-55° C.

Aufarbeitung

  1. temperatureto reflux in a nitrogen atmosphere, whereupon the temperature
  2. customrises to 118° C
  3. temperatureAfter a reaction time of 6 hours, the reaction mixture is cooled
  4. filtrationfiltered
  5. customThe organic phase is separated in a separating funnel
  6. washthe aqueous phase is washed once more with ethyl acetate
  7. washThe combined organic extracts (ethyl acetate extracts) are washed with a solution of sodium chloride
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customthe solution is purified by chromatography through a column
  11. washAfter elution with toluene, concentration of the

Quellen und Nachweise

ORD-Eintrag
ord-96492b177b704c0e92dfccf1f0e727b1
Quelldatensatz
uspto-grants-1980_06
Patentnummer
US04206152

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