Chloroform → 1-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde

HRID 131647

Reaktionsgleichung

Reaktionsgleichung von HRID 131647
P(Cl)(Cl)(Cl)=O.CN(C)C=O.[CH:11]([Cl:14])(Cl)Cl.C[C:16]1[CH:25]=[C:24](C)[CH:23]=[C:22]2[C:17]=1[CH2:18][CH2:19][CH2:20][C:21]2=[O:27]>O>[Cl:14][C:11]1[C:22]2[C:17](=[CH:16][CH:25]=[CH:24][CH:23]=2)[CH2:18][CH2:19][C:20]=1[CH:21]=[O:27]

Komponenten

6

Edukt 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 836193,4-dihydro-5,7-dimethylnaphthalen-1(2H)-one

Produkt 1

HCID 767521-Chloro-3,4-dihydronaphthalene-2-carboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1.3 mL of phosphorus oxychloride was added dropwise to 1.6 mL of dimethylformamide under ice cooling, after which the system was brought up to room temperature and stirred for 30 minutes. To this was added at room temperature a 50 mL chloroform solution of 1.8 g of 5,7-dimethyltetralone, and the system was refluxed under heating overnight. After the reaction, water was added and the system was stirred for 30 minutes, after which the organic layer was washed first with a saturated sodium hydrogencarbonate aqueous solution and then with saturated brine, dried with magnesium sulfate, and then subjected to reduced-pressure solvent distillation, and the residue was refined by silica gel column chromatography (5% ethyl acetate/hexane) to obtain 2.0 g of 1-chloro-2-formyl-3,4-dihydronaphthalene in the form of a brown solid.

Aufarbeitung

  1. customwas brought up to room temperature
  2. temperaturethe system was refluxed
  3. temperatureunder heating overnight
  4. additionwas added
  5. stirringthe system was stirred for 30 minutes
  6. washafter which the organic layer was washed first with a saturated sodium hydrogencarbonate aqueous solution
  7. dry with materialwith saturated brine, dried with magnesium sulfate
  8. distillationsubjected to reduced-pressure solvent distillation

Quellen und Nachweise

ORD-Eintrag
ord-bb7d241bd498490e8b874b95f3cb2a98
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384974B2

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