1-Chloromethylnaphthalene → 2-(Naphthalen-1-ylmethoxy)benzaldehyde

HRID 1795113

Reaktionsgleichung

Reaktionsgleichung von HRID 1795113
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Cl[CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[C:12]1([CH2:11][O:1][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 68451-ChloromethylnaphthaleneHCID 6998SalicylaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Produkt 1

HCID 8854962-(Naphthalen-1-ylmethoxy)benzaldehydeAusbeute 43,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 2-hydroxybenzaldehyde (2.30 g, 18.8 mmol) in DMF (20 mL) is added 1-(chloromethyl)-naphthalene (3.36 mL, 22.6 mmol) and K2CO3 (3.11 g, 22.6 mmol), and the reaction mixture is heated to 100° C. for 12 h. Once complete, the reaction mixture is cooled to room temperature and diluted with water (100 mL) prior to being poured into a separatory funnel containing ethyl acetate (250 mL). The organic layer is separated, washed with brine (2×) and dried over sodium sulfate prior to concentration. The crude product is purified by column chromatography (5% ethyl acetate in hexanes) to afford 2-(1-naphthylmethoxy)benzaldehyde (2.13 g, 43%) as a light yellow oil.

Aufarbeitung

  1. temperatureOnce complete, the reaction mixture is cooled to room temperature
  2. additionto being poured into a separatory funnel
  3. customThe organic layer is separated
  4. washwashed with brine (2×)
  5. dry with materialdried over sodium sulfate
  6. concentrationto concentration
  7. customThe crude product is purified by column chromatography (5% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3f39b2fc764a4dc582d690e962a26da4
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07026339B2

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