p-(Trifluoromethoxy)benzaldehyde → 4-(Trifluoromethoxy)benzenemethanol

HRID 991281

Reaktionsgleichung

Reaktionsgleichung von HRID 991281
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.C([O-])=O.[Na+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C>[F:1][C:2]([F:12])([F:13])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 2723810Sodium Formate

Produkt 1

HCID 1371844-(Trifluoromethoxy)benzenemethanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

8.55 g of 4-trifluoromethoxybenzaldehyde, 0.63 g of bis(triphenylphosphine) palladium dichloride and 6.12 g of sodium formate were placed in a flask fitted with a reflux condenser, 45 ml of DMF were added and the mixture was stirred and heated at 110° C. The course of the reaction was monitored by means of GC. After conversion was complete (GC monitoring), the reaction mixture was allowed to cool to 21° C. and the catalyst was separated off by filtration through silica gel. The filter was rinsed with methyl tert-butyl ether and the filtrate washed with 3×100 ml of water in order to remove the DMF. This gave 6.0 g (69% of theory) of 4-trifluoromethoxybenzyl alcohol.

Aufarbeitung

  1. customfitted with a reflux condenser
  2. temperatureto cool to 21° C.
  3. customthe catalyst was separated off by filtration through silica gel
  4. washThe filter was rinsed with methyl tert-butyl ether
  5. washthe filtrate washed with 3×100 ml of water in order
  6. customto remove the DMF

Quellen und Nachweise

ORD-Eintrag
ord-b679be3d4e484e96b9d1d463d6c43255
Quelldatensatz
uspto-grants-2002_10
Patentnummer
US06462242B1

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